David Crich

Summary

Affiliation: Avenue de la Terrasse
Country: France

Publications

  1. doi Epimerization-free block synthesis of peptides from thioacids and amines with the Sanger and Mukaiyama reagents
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202, USA
    Angew Chem Int Ed Engl 48:2355-8. 2009
  2. pmc Stereocontrolled synthesis of D- and L-beta-rhamnopyranosides with 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycosides
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    J Org Chem 74:773-81. 2009
  3. pmc The 4-(tert-butyldiphenylsiloxy)-3-fluorobenzyl group: a new alcohol protecting group, fully orthogonal with the p-methoxybenzyl group and removable under desilylation conditions
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    J Org Chem 74:2486-93. 2009
  4. doi S(N)2-type nucleophilic opening of beta-thiolactones (thietan-2-ones) as a source of thioacids for coupling reactions
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    J Org Chem 74:3389-93. 2009
  5. pmc Thiomaleic anhydride: a convenient building block for the synthesis of alpha-substituted gamma- and delta-lactones through free-radical addition, nucleophilic ring opening, and subsequent thiocarboxylate manipulation
    David Crich
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    J Org Chem 74:6792-6. 2009
  6. pmc Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors
    David Crich
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    J Org Chem 75:8383-91. 2010
  7. pmc Reaction of thioacids with isocyanates and isothiocyanates: a convenient amide ligation process
    David Crich
    Centre Scientifique de Gif, Institut de Chimie des Substances Naturelles, 1 Avenue de la Terrasse, 91198 Gif sur Yvette, France
    Org Lett 11:3514-7. 2009
  8. doi Mechanism of a chemical glycosylation reaction
    David Crich
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    Acc Chem Res 43:1144-53. 2010
  9. pmc Highly stereoselective synthesis of alpha-D-mannopyranosyl phosphosugars
    David Crich
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198 Gif sur Yvette, France
    J Org Chem 74:9576-9. 2009
  10. pmc Silver-mediated allylic disulfide rearrangement for conjugation of thiols in protic media
    David Crich
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    J Org Chem 74:9422-7. 2009

Collaborators

Detail Information

Publications86

  1. doi Epimerization-free block synthesis of peptides from thioacids and amines with the Sanger and Mukaiyama reagents
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202, USA
    Angew Chem Int Ed Engl 48:2355-8. 2009
    ..This essentially epimerization-free method was used for the 4+4 block synthesis of a hindered octapeptide (see scheme; Boc, Pbf, and Trt are protecting groups)...
  2. pmc Stereocontrolled synthesis of D- and L-beta-rhamnopyranosides with 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycosides
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    J Org Chem 74:773-81. 2009
    ..Following desulfurization and concomitant debenzylation with Raney nickel, the so-formed 6-thio-beta-mannosides are converted in high yield to the beta-rhamnopyranosides...
  3. pmc The 4-(tert-butyldiphenylsiloxy)-3-fluorobenzyl group: a new alcohol protecting group, fully orthogonal with the p-methoxybenzyl group and removable under desilylation conditions
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    J Org Chem 74:2486-93. 2009
    ..Applications of the new protecting group in the direct stereocontrolled synthesis of beta-mannopyranosides are presented...
  4. doi S(N)2-type nucleophilic opening of beta-thiolactones (thietan-2-ones) as a source of thioacids for coupling reactions
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    J Org Chem 74:3389-93. 2009
    ..In another embodiment, the thiocarboxylate intermediate is allowed to react with a sulfonyl azide, resulting overall in N-arenesulfonyl 3-arylthiopropionamide derivatives...
  5. pmc Thiomaleic anhydride: a convenient building block for the synthesis of alpha-substituted gamma- and delta-lactones through free-radical addition, nucleophilic ring opening, and subsequent thiocarboxylate manipulation
    David Crich
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    J Org Chem 74:6792-6. 2009
    ....
  6. pmc Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors
    David Crich
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    J Org Chem 75:8383-91. 2010
    ....
  7. pmc Reaction of thioacids with isocyanates and isothiocyanates: a convenient amide ligation process
    David Crich
    Centre Scientifique de Gif, Institut de Chimie des Substances Naturelles, 1 Avenue de la Terrasse, 91198 Gif sur Yvette, France
    Org Lett 11:3514-7. 2009
    ..A carboxylate salt is also shown to react with an electron-deficient isocyanate to give the corresponding amide in excellent yield at room temperature...
  8. doi Mechanism of a chemical glycosylation reaction
    David Crich
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    Acc Chem Res 43:1144-53. 2010
    ....
  9. pmc Highly stereoselective synthesis of alpha-D-mannopyranosyl phosphosugars
    David Crich
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198 Gif sur Yvette, France
    J Org Chem 74:9576-9. 2009
    ..Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed...
  10. pmc Silver-mediated allylic disulfide rearrangement for conjugation of thiols in protic media
    David Crich
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    J Org Chem 74:9422-7. 2009
    ..The silver-mediated reaction functions at ambient temperature in protic solvents and in the absence of protecting groups...
  11. doi One-pot syntheses of dissymmetric diamides based on the chemistry of cyclic monothioanhydrides. Scope and limitations and application to the synthesis of glycodipeptides
    David Crich
    Centre de Recherche CNRS de Gif sur Yvette, Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    J Org Chem 74:3886-93. 2009
    ....
  12. pmc Solid-phase synthesis of peptidyl thioacids employing a 9-fluorenylmethyl thioester-based linker in conjunction with Boc chemistry
    David Crich
    Centre de Recherche de Gif sur Yvette, Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    J Org Chem 74:7383-8. 2009
    ..The so-obtained thioacids are converted to simple thioesters in high yield by standard alkylation according to well-established methods...
  13. pmc Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyran
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Am Chem Soc 128:8078-86. 2006
    ....
  14. ncbi Synthesis and glycosylation of a series of 6-mono-, di-, and trifluoro S-phenyl 2,3,4-tri-O-benzyl-thiorhamnopyranosides. Effect of the fluorine substituents on glycosylation stereoselectivity
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Am Chem Soc 129:11756-65. 2007
    ..The results are explained with regard to the increased stability of the glycosyl triflates, shown to be intermediates in the reaction by low-temperature 1H NMR experiments, with increased fluorine content...
  15. doi Highly stereoselective synthesis of primary, secondary, and tertiary α-S-sialosides under Lewis acidic conditions
    Amandine Noël
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif sur Yvette, France
    Org Lett 14:4138-41. 2012
    ..The reactions, which proceed under typical Lewis acid promoted glycosylation conditions, are highly α-selective and do not suffer from competing elimination of the phosphate...
  16. pmc Dechalcogenative allylic selenosulfide and disulfide rearrangements: complementary methods for the formation of allylic sulfides in the absence of electrophiles. Scope, limitations, and application to the functionalization of unprotected peptides in aqueo
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Am Chem Soc 129:10282-94. 2007
    ..Under these latter conditions the reaction is also applicable to allyl aryl disulfides, providing allylically rearranged allyl aryl sulfides in good yields...
  17. pmc On the use of 3,5-O-benzylidene and 3,5-O-(di-tert-butylsilylene)-2-O-benzylarabinothiofuranosides and their sulfoxides as glycosyl donors for the synthesis of beta-arabinofuranosides: importance of the activation method
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607 7061, USA
    J Org Chem 72:1553-65. 2007
    ....
  18. pmc Direct stereocontrolled synthesis of 3-amino-3-deoxy-beta-mannopyranosides: importance of the nitrogen protecting group on stereoselectivity
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 72:5183-92. 2007
    ..The reasons for the protecting group dependency are discussed in terms of the change in the O2-C2-C3-N3 torsional interaction on conversion of the covalent glycosyl triflates to the transient oxacarbenium ions...
  19. pmc 4,6-O-benzylidene-directed beta-mannopyranosylation and alpha-glucopyranosylation: the 2-deoxy-2-fluoro and 3-deoxy-3-fluoro series of donors and the importance of the O2-C2-C3-O3 interaction
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607 7061, USA
    J Org Chem 72:1681-90. 2007
    ....
  20. doi Comparison of the reactivity of β-thiolactones and β-lactones toward ring-opening by thiols and amines
    Amandine Noël
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif sur Yvette, France
    Org Biomol Chem 10:6480-3. 2012
    ..Implications for the use of β-thiolactones in bioorganic and medicinal chemistry are discussed...
  21. pmc Protecting group-free glycoligation by the desulfurative rearrangement of allylic disulfides as a means of assembly of oligosaccharide mimetics
    Venkataraman Subramanian
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States
    J Org Chem 76:3691-709. 2011
    ..Variations on the general theme enable the preparation of mimetics of reducing and nonreducing oligosaccharides as well as of nonglycosidically linked systems...
  22. pmc Cation clock permits distinction between the mechanisms of α- and β-O- and β-C-glycosylation in the mannopyranose series: evidence for the existence of a mannopyranosyl oxocarbenium ion
    Min Huang
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif sur Yvette, France
    J Am Chem Soc 134:14746-9. 2012
    ..Relative rate constants for reactions going via a common intermediate can be estimated...
  23. doi Influence of protecting groups on the reactivity and selectivity of glycosylation: chemistry of the 4,6-o-benzylidene protected mannopyranosyl donors and related species
    Sylvain Aubry
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198, Gif sur Yvette, France
    Top Curr Chem 301:141-88. 2011
    ....
  24. pmc Facile oxidative cleavage of 4-O-benzyl ethers with dichlorodicyanoquinone in rhamno- and mannopyranosides
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 72:3581-4. 2007
    ..On exposure to dichlorodicyanoquinone in wet dichloromethane at room temperature, equatorial 4-O-benzyl ethers are removed with moderate selectivity in the presence of other benzyl ethers in glycopyranosides and glycothiopyranosides...
  25. pmc Synthesis of neoglycoconjugates by the desulfurative rearrangement of allylic disulfides
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    J Org Chem 73:7017-27. 2008
    ..The conjugation reaction functions in the absence of protecting groups on both the neoglycosyl donor and peptide in aqueous media at room temperature...
  26. pmc Is donor-acceptor hydrogen bonding necessary for 4,6-O-benzylidene-directed beta-mannopyranosylation? Stereoselective synthesis of beta-C-mannopyranosides and alpha-C-glucopyranosides
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    Org Lett 10:4731-4. 2008
    ..This selectivity pattern parallels that of O-glycoside formation and eliminates the need to consider donor-acceptor hydrogen bonding in the formation of the O-glycosides...
  27. pmc Dimethylthexylsilyl 2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-beta-D-glucopyranoside, dimethylthexylsilyl 3,4,6-tri-O-benzyl-beta-D-mannopyranosyl-(1-->4)-2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-beta-D-glucopyranoside, and dimethy
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202, USA
    Carbohydr Res 344:140-4. 2009
    ..Sulfonylation then gave dimethylthexylsilyl 2-O-(benzylsulfonyl)-3,4,6-tri-O-benzyl-beta-D-mannopyranosyl-(1-->4)-2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-beta-D-glucopyranoside...
  28. ncbi 4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetals. improved second-generation acetals for the stereoselective formation of beta-D-mannopyranosides and regioselective reductive radical fragmentation to beta-D-rhamnopyranosides. scope and limitations
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 71:3452-63. 2006
    ..Variable-temperature NMR studies for the glycosylation step, which helped define an optimal protocol, are described...
  29. ncbi The 3,4-O-carbonate protecting group as a beta-directing group in rhamnopyranosylation in both homogeneous and heterogeneous glycosylations as compared to the chameleon-like 2,3-O-carbonates
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 68:8453-8. 2003
    ....
  30. pmc Probing the influence of a 4,6-O-acetal on the reactivity of galactopyranosyl donors: verification of the disarming influence of the trans-gauche conformation of C5-C6 bonds
    Myriame Moumé-Pymbock
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States
    J Am Chem Soc 135:14249-55. 2013
    ..Reasons for the α-selectivity of 4,6-O-benzylidene-protected galactopyranosyl donors bearing neighboring group-active protecting groups at O2 are discussed. ..
  31. doi Alternative synthesis of P-chiral phosphonite-borane complexes: application to the synthesis of phostone-phostone dimers
    Angélique Ferry
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    J Org Chem 78:6858-67. 2013
    ..This direct P(III) strategy facilitates the obtention of various P-chiral phosphonite-boranes, of which further coupling reactions are described leading to the selective synthesis of two phostone dimers. ..
  32. doi N-O bond as a glycosidic-bond surrogate: synthetic studies toward polyhydroxylated N-alkoxypiperidines
    Gaëlle Malik
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    Chemistry 19:2168-79. 2013
    ..With the exception of N-hydroxyisofagomine itself, none of the compounds prepared showed significant inhibitory activity against sweet almond β-glucosidase...
  33. pmc Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series
    Indrajeet Sharma
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202, USA
    Carbohydr Res 357:126-31. 2012
    ..The phenomenon is considered to arise from the lower steric bulk of the benzylidene acetal that, through diminished buttressing interactions, reduces steric interactions normally present in the β-anomer...
  34. ncbi Synthesis of the Salmonella type E(1) core trisaccharide as a probe for the generality of 1-(benzenesulfinyl)piperidine/triflic anhydride combination for glycosidic bond formation from thioglycosides
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 67:4640-6. 2002
    ..2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyl thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions...
  35. ncbi Cyclic thioanhydrides: linchpins for multicomponent coupling reactions based on the reaction of thioacids with electron-deficient sulfonamides and azides
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48230, USA
    Org Lett 9:5323-5. 2007
    ..The use of thiomaleic anhydride and a bifunctional nucleophile extends the process to heterocycle synthesis, while a cyclic thioanhydride prepared from aspartic acid directly provides N-functionalized asparagine derivatives...
  36. pmc Direct Fmoc-chemistry-based solid-phase synthesis of peptidyl thioesters
    Indrajeet Sharma
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    J Org Chem 76:6518-24. 2011
    ..Subsequent S-alkylation of the thioamide gives a thioimide that, on treatment with aqueous trifluoroacetic acid, releases the peptide from the resin in the form of a C-terminal thioester...
  37. ncbi Mechanism of 4,6-O-benzylidene-directed beta-mannosylation as determined by alpha-deuterium kinetic isotope effects
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607 7061, USA
    Angew Chem Int Ed Engl 43:5386-9. 2004
  38. pmc alpha-selective sialylations at -78 degrees C in nitrile solvents with a 1-adamantanyl thiosialoside
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 72:7794-7. 2007
    ....
  39. ncbi 6-O-Benzyl- and 6-O-silyl-N-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxyglucosides: effective glycosyl acceptors in the glucosamine 4-OH Series. effect of anomeric stereochemistry on the removal of the oxazolidinone group
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 70:1291-6. 2005
    ....
  40. ncbi Chemistry of the Hexahydropyrrolo[2,3-b]indoles: configuration, conformation, reactivity, and applications in synthesis
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    Acc Chem Res 40:151-61. 2007
    ..The use of the tryptophan-derived hexahydro[2,3-b]pyrroloindoles in the stereocontrolled synthesis of amino acids and alkaloids is presented...
  41. ncbi Allylic disulfide rearrangement and desulfurization: mild, electrophile-free thioether formation from thiols
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    Org Lett 8:3593-6. 2006
    ..On the addition of a phosphine, a desulfurative sigmatropic rearrangement takes place at room temperature to give thioethers...
  42. pmc Sigmatropic rearrangements as tools for amino acid and peptide modification: application of the allylic sulfur ylide rearrangement to the preparation of neoglycoconjugates and other conjugates
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 71:9172-7. 2006
    ..The reaction is successfully applied to the introduction of lipid-like residues, a fluorous alkyl chain, and mono- and disaccharides...
  43. pmc On the influence of the C2-O2 and C3-O3 bonds in 4,6-O-benzylidene-directed beta-mannopyranosylation and alpha-glucopyranosylation
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 71:8473-80. 2006
    ....
  44. doi Synthesis and evaluation of 3-deoxy and 3-deoxy-3-fluoro derivatives of gluco- and manno-configured tetrahydropyridoimidazole glycosidase inhibitors
    Cécile Ouairy
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Gif sur Yvette, France
    Carbohydr Res 377:35-43. 2013
    ....
  45. doi Synthesis and biological investigation of the β-thiolactone and β-lactam analogs of tetrahydrolipstatin
    Sylvain Aubry
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif sur Yvette, France
    Org Biomol Chem 10:2629-32. 2012
    ..These analogs, and a cis-disubstituted β-lactone analog of tetrahydrolipstatin, were screened for activity against porcine pancreatic lipase and for inhibition of cell growth of a panel of four human cancer lines...
  46. pmc Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry
    David Crich
    Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA
    J Org Chem 76:9193-209. 2011
    ....
  47. ncbi Influence of the 4,6-O-benzylidene, 4,6-O-phenylboronate, and 4,6-O-polystyrylboronate protecting groups on the stereochemical outcome of thioglycoside-based glycosylations mediated by 1-benzenesulfinyl piperidine/triflic anhydride and N-iodosuccinimide/t
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 68:8142-8. 2003
    ....
  48. ncbi The 4,6-O-[alpha-(2-(2- iodophenyl)ethylthiocarbonyl)benzylidene] protecting group: stereoselective glycosylation, reductive radical fragmentation, and synthesis of beta-D-rhamnopyranosides and other deoxy sugars
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    Org Lett 5:2189-91. 2003
    ..The radical fragmentation is fully compatible with the presence of benzyl and p-methoxybenzyl ethers and with acetate esters..
  49. pmc Convergent synthesis of a beta-(1-->3)-mannohexaose
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 72:6806-15. 2007
    ..Comparison of three closely related attempted mannohexaose syntheses reinforces the influence of subtle matching and/or mismatching interactions on the outcome of convergent oligosaccharide synthesis...
  50. ncbi Benzylidene acetal fragmentation route to 6-deoxy sugars: direct reductive cleavage in the presence of ether protecting groups, permitting the efficient, highly stereocontrolled synthesis of beta-D-rhamnosides from D-mannosyl glycosyl donors. Total synthe
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607 7061, USA
    J Am Chem Soc 126:8232-6. 2004
    ....
  51. ncbi Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 71:3064-70. 2006
    ..Deprotection is achieved by base-catalyzed isomerization of the propargyl ether group to the corresponding allenyl ether, followed by oxidative cleavage with N-methylmorpholine N-oxide and catalytic osmium tetroxide...
  52. ncbi Synthesis of N-acyl-5-aminopenta-2,4-dienals via base-induced ring-opening of N-acylated furfurylamines: scope and limitations
    Cécile Ouairy
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette Cedex, France
    J Org Chem 75:4311-4. 2010
    ..The efficacy of the reaction was shown to be very dependent on the nature of these groups...
  53. ncbi Synthesis and stereoselective glycosylation of D- and L-glycero-beta-D-manno-heptopyranoses
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    Org Lett 7:1395-8. 2005
    ..The method relies on the presence of a 4,6-O-benzylidene acetal to effect stereocontrol at the anomeric center; the configuration at C6 (L- or D-glycero) is of minimal importance...
  54. ncbi 2-O-propargyl ethers: readily cleavable, minimally intrusive protecting groups for beta-mannosyl donors
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    Org Lett 7:2277-80. 2005
    ..Deprotection is conducted by treatment with potassium tert-butoxide followed by catalytic osmium tetroxide and N-methylmorpholine N-oxide...
  55. pmc Stereoselective C-glycoside formation with 2-O-benzyl-4,6-O-benzylidene protected 3-deoxy gluco- and mannopyranoside donors: comparison with O-glycoside formation
    Myriame Moumé-Pymbock
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    J Org Chem 77:8905-12. 2012
    ....
  56. doi Stereoselective, electrophilic α-C-sialidation
    Amandine Noël
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif sur Yvette, France
    Org Lett 14:1342-5. 2012
    ..Elimination to give the 2,3-glycal is minimized by the presence of the oxazolidinone ring. The oxazolidinone ring can be subsequently cleaved under mild conditions at room temperature leaving in place the native acetamide group...
  57. doi Exploring the potential of the β-thiolactones in bioorganic chemistry
    Sylvain Aubry
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190, Gif sur Yvette, France
    Org Biomol Chem 9:7134-43. 2011
    ..Several of the β-thiolactones prepared showed strong inhibitory activity in vitro against human cathepsins B and L...
  58. pmc Synthesis and structural verification of the xylomannan antifreeze substance from the freeze-tolerant Alaskan beetle Upis ceramboides
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States
    J Org Chem 76:8611-20. 2011
    ....
  59. doi Facile amide bond formation from carboxylic acids and isocyanates
    Kaname Sasaki
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif sur Yvette, France
    Org Lett 13:2256-9. 2011
    ..The reaction is compatible with hydroxyl groups and both Fmoc and Boc protecting groups for amines and is applicable to aliphatic, aromatic, and heteroaromatic acids...
  60. doi One-pot formation of piperidine- and pyrrolidine-substituted pyridinium salts via addition of 5-alkylaminopenta-2,4-dienals to N-acyliminium ions: application to the synthesis of (±)-nicotine and analogs
    Sabrina Peixoto
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette Cedex, France
    Org Lett 12:4760-3. 2010
    ..Subsequent N-dealkylation of the pyridinium moiety and deprotection of the secondary amine or reduction of the carbamate function led to (±)-nicotine and analogs...
  61. pmc O-sialylation with N-acetyl-5-n,4-o-carbonyl-protected thiosialoside donors in dichloromethane: facile and selective cleavage of the oxazolidinone ring
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 72:2387-91. 2007
    ..The oxazolidinone of the N-acetyl-5-N,4-O-carbonyl protected sialosides, both alpha- and beta-anomers, could be cleaved cleanly by treatment with sodium methoxide under mild conditions without removal of the acetamide...
  62. ncbi Expedient two-step synthesis of phenolic cyclitols from benzene
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 71:4521-4. 2006
    ....
  63. ncbi Native chemical ligation at phenylalanine
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Am Chem Soc 129:10064-5. 2007
  64. ncbi Amino acid and peptide synthesis and functionalization by the reaction of thioacids with 2,4-dinitrobenzenesulfonamides
    David Crich
    Chemistry Department, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    Org Lett 9:4423-6. 2007
    ..When the sulfonamide is derived from an amino acid the method results in peptide bond formation, whereas the use of carbohydrate derived sulfonamides gives neoglycoconjugates...
  65. pmc A stable, commercially available sulfenyl chloride for the activation of thioglycosides in conjunction with silver trifluoromethanesulfonate
    David Crich
    Department of Chemistry, Wayne State University, Detroit, MI 48202, USA
    Carbohydr Res 343:1858-62. 2008
    ..p-Nitrobenzenesulfenyl chloride is a stable commercially available sulfenyl chloride that, in conjunction with silver triflate, cleanly activates a wide range of thioglycosides for glycosylation at -78 degrees C in CH(2)Cl(2)...
  66. ncbi Direct chemical synthesis of the beta-mannans: linear and block syntheses of the alternating beta-(1-->3)-beta-(1-->4)-mannan common to Rhodotorula glutinis, Rhodotorula mucilaginosa, and Leptospira biflexa
    David Crich
    Department of Chemistry, University of Illinois, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Am Chem Soc 126:15081-6. 2004
    ..9%. The second synthesis, a block synthesis, makes use of the coupling of two trisaccharides, resulting in a shorter sequence and an overall yield of 4.4%, despite the poor selectivity in the key step...
  67. pmc Stereoselective iterative one-pot synthesis of N-glycolylneuraminic acid-containing oligosaccharides
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    Org Lett 10:4033-5. 2008
    ..The use of an N-acyloxazolidinone-protected S-adamantanyl thiosialoside allows the highly stereoselective, one-pot multicomponent synthesis of alpha-sialoside-based oligosaccharides...
  68. pmc Block synthesis of tetra- and hexasaccharides (beta-D-glycero-D-manno-Hep p-(1-->4)-[alpha-l-Rha p-(1-->3)-beta-D-glycero-D-manno-Hep p-(1-->4)]n-alpha-L-Rha p-OMe (n = 1 and 2)) corresponding to multiple repeat units of the glycan from the surfa
    David Crich
    Chemistry Department, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    J Org Chem 73:7003-10. 2008
    ..Comparison of the spectral data for the hexasaccharide with that of the natural isolate confirms the structure of this very unusual and structurally challenging glycan...
  69. pmc Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediates
    David Crich
    Chemistry Department, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    J Org Chem 73:8942-53. 2008
    ....
  70. pmc Expedient synthesis of threo-beta-hydroxy-alpha-amino acid derivatives: phenylalanine, tyrosine, histidine, and tryptophan
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607 7061, USA
    J Org Chem 71:7106-9. 2006
    ..Cesium carbonate catalyzed hydrolysis then generated the beta-hydroxy amino acid derivatives in excellent overall yield...
  71. ncbi Allylic selenosulfide rearrangement: a method for chemical ligation to cysteine and other thiols
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 60607 7061, USA
    J Am Chem Soc 128:2544-5. 2006
    ..The process is illustrated through the lipidation of cysteine-containing tripeptides and by the allylation of 1-thioglucose tetraacetate...
  72. pmc Efficient glycosidation of a phenyl thiosialoside donor with diphenyl sulfoxide and triflic anhydride in dichloromethane
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    Org Lett 8:959-62. 2006
    ..With an excess of diphenyl sulfoxide, glycal formation can be completely suppressed and excellent yields are obtained for coupling to a wide range of primary, secondary, and tertiary acceptors...
  73. doi Cyclic peptide synthesis with thioacids
    Kaname Sasaki
    Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette, France
    Org Lett 12:3254-7. 2010
    ..Cyclic penta- and hexapeptides have been synthesized in this manner, as has a cyclic glycopeptide. Functional group compatibility with alcohols and carboxylic acids is demonstrated...
  74. pmc Synthesis of a beta-(1-->3)-D-rhamnotetraose by a one-pot, multiple radical fragmentation
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    Org Lett 8:4327-30. 2006
    ..The route is concise, proceeding through a late-stage radical deoxygenation that successfully uncovers all four deoxy subunits at once...
  75. pmc 1-naphthylpropargyl ether group: a readily cleaved and sterically minimal protecting system for stereoselective glycosylation
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    Org Lett 8:4879-82. 2006
    ..In conjunction with the 4,6-O-benzylidene protecting group, and the use of the sulfoxide glycosylation method, 3-O-naphthylpropargyl-protected mannosyl donors are extremely beta-selective...
  76. pmc Stereocontrolled glycoside and glycosyl ester synthesis. neighboring group participation and hydrogenolysis of 3-(2'-benzyloxyphenyl)-3,3-dimethylpropanoates
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    Org Lett 9:1613-5. 2007
    ....
  77. pmc Revisiting the armed-disarmed concept: the importance of anomeric configuration in the activation of S-benzoxazolyl glycosides
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    Org Lett 9:4115-8. 2007
    ..Revision of the armed-disarmed concept for glycosyl donors is not required...
  78. pmc Application of the 4-trifluoromethylbenzenepropargyl ether group as an unhindered, electron deficient protecting group for stereoselective glycosylation
    David Crich
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA
    J Org Chem 73:5173-6. 2008
    ..In conjunction with the 4,6-O-benzylidene protecting group, glycosylation reactions of 2-O-(4-trifluoromethylbenzenepropargyl)-protected mannosyl donors are extremely beta-selective...
  79. ncbi Solid-phase synthesis of beta-mannosides
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Am Chem Soc 124:8867-9. 2002
    ..Successful, diastereoselective coupling is demonstrated with a range of primary, secondary, and tertiary glycosyl acceptors, including typical carbohydrates and threonine derivatives...
  80. ncbi Oxazolidinone protection of N-acetylglucosamine confers high reactivity on the 4-hydroxy group in glycosylation
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    Org Lett 5:1297-300. 2003
    ..This substance exhibits enhanced reactivity as a glycosyl acceptor in a variety of coupling methods, the products of which are converted to the target N-acetylglucosaminyl saccharides under very mild conditions...
  81. ncbi Stereocontrolled formation of beta-glucosides and related linkages in the absence of neighboring group participation: influence of a trans-fused 2,3-O-carbonate group
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Org Chem 70:7252-9. 2005
    ....
  82. pmc On the nitrile effect in L-rhamnopyranosylation
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607 7061, USA
    Carbohydr Res 341:1467-75. 2006
    ..The use of more significant quantities of acetonitrile or propionitrile results in the formation of complex reaction mixtures containing little coupled product, but from which Ritter-type products can be isolated...
  83. ncbi Direct synthesis of the beta-l-rhamnopyranosides
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    Org Lett 5:781-4. 2003
    ..Selectivities vary from moderate to good, and the sulfonyl group is easily removed post-glycosylation with sodium amalgam in 2-propanol...
  84. ncbi Confirmation of the connectivity of 4,8,12,16,20-pentamethylpentacosylphoshoryl beta-D-mannopyranoside, an unusual beta-mannosyl phosphoisoprenoid from Mycobacterium avium, through synthesis
    David Crich
    Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607 7061, USA
    J Am Chem Soc 124:2263-6. 2002
    ....
  85. ncbi Stereoselective formation of glycosyl sulfoxides and their subsequent equilibration: ring inversion of an alpha-xylopyranosyl sulfoxide dependent on the configuration at sulfur
    David Crich
    Department of Chemistry, University of Illinois at Chicago, Chicago, Illinois 60607 7061, USA
    J Am Chem Soc 124:6028-36. 2002
    ....
  86. ncbi Total synthesis and structural verification of some novel branched alkanes with quaternary carbons isolated from diverse geological sources
    David Crich
    Department of Chemistry, University of Illinois at Chicago, Chicago, Illinois 60607 7061, USA
    J Org Chem 71:5016-9. 2006
    ..However, the GC-MS data of the two more highly branched structures do not match those of the geological isolates leading to the conclusion that these structures were erroneously assigned...