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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

David Crich

Department of Chemistry

University of Illinois at Chicago

845 West Taylor Street




Name/email consistency: high



  • Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, USA. 2000 - 2007


  1. 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. Crich, D., Pedersen, C.M., Bowers, A.A., Wink, D.J. J. Org. Chem. (2007) [Pubmed]
  2. Direct stereocontrolled synthesis of 3-amino-3-deoxy-beta-mannopyranosides: importance of the nitrogen protecting group on stereoselectivity. Crich, D., Xu, H. J. Org. Chem. (2007) [Pubmed]
  3. Catalysis of stannane-mediated radical chain reactions by benzeneselenol. Crich, D., Grant, D., Krishnamurthy, V., Patel, M. Acc. Chem. Res. (2007) [Pubmed]
  4. Facile oxidative cleavage of 4-O-benzyl ethers with dichlorodicyanoquinone in rhamno- and mannopyranosides. Crich, D., Vinogradova, O. J. Org. Chem. (2007) [Pubmed]
  5. 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. Crich, D., Li, L. J. Org. Chem. (2007) [Pubmed]
  6. O-sialylation with N-acetyl-5-n,4-o-carbonyl-protected thiosialoside donors in dichloromethane: facile and selective cleavage of the oxazolidinone ring. Crich, D., Li, W. J. Org. Chem. (2007) [Pubmed]
  7. Stereocontrolled glycoside and glycosyl ester synthesis. neighboring group participation and hydrogenolysis of 3-(2'-benzyloxyphenyl)-3,3-dimethylpropanoates. Crich, D., Cai, F. Org. Lett. (2007) [Pubmed]
  8. Total synthesis and structural verification of some novel branched alkanes with quaternary carbons isolated from diverse geological sources. Crich, D., Xu, H., Kenig, F. J. Org. Chem. (2006) [Pubmed]
  9. Allylic selenosulfide rearrangement: a method for chemical ligation to cysteine and other thiols. Crich, D., Krishnamurthy, V., Hutton, T.K. J. Am. Chem. Soc. (2006) [Pubmed]
  10. Efficient glycosidation of a phenyl thiosialoside donor with diphenyl sulfoxide and triflic anhydride in dichloromethane. Crich, D., Li, W. Org. Lett. (2006) [Pubmed]
  11. On the regioselectivity of the Hanessian-Hullar reaction in 4,6-O-benzylidene protected galactopyranosides. Crich, D., Yao, Q., Bowers, A.A. Carbohydr. Res. (2006) [Pubmed]
  12. Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups. Crich, D., Jayalath, P., Hutton, T.K. J. Org. Chem. (2006) [Pubmed]
  13. 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. Crich, D., Bowers, A.A. J. Org. Chem. (2006) [Pubmed]
  14. On the nitrile effect in L-rhamnopyranosylation. Crich, D., Patel, M. Carbohydr. Res. (2006) [Pubmed]
  15. Expedient two-step synthesis of phenolic cyclitols from benzene. Crich, D., Grant, D., Wink, D.J. J. Org. Chem. (2006) [Pubmed]
  16. 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-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides. Crich, D., Banerjee, A. J. Am. Chem. Soc. (2006) [Pubmed]
  17. Allylic disulfide rearrangement and desulfurization: mild, electrophile-free thioether formation from thiols. Crich, D., Brebion, F., Krishnamurthy, V. Org. Lett. (2006) [Pubmed]
  18. Expedient synthesis of threo-beta-hydroxy-alpha-amino acid derivatives: phenylalanine, tyrosine, histidine, and tryptophan. Crich, D., Banerjee, A. J. Org. Chem. (2006) [Pubmed]
  19. Synthesis of a beta-(1-->3)-D-rhamnotetraose by a one-pot, multiple radical fragmentation. Crich, D., Bowers, A.A. Org. Lett. (2006) [Pubmed]
  20. 1-naphthylpropargyl ether group: a readily cleaved and sterically minimal protecting system for stereoselective glycosylation. Crich, D., Wu, B. Org. Lett. (2006) [Pubmed]
  21. On the influence of the C2-O2 and C3-O3 bonds in 4,6-O-benzylidene-directed beta-mannopyranosylation and alpha-glucopyranosylation. Crich, D., Vinogradova, O. J. Org. Chem. (2006) [Pubmed]
  22. 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. Crich, D., Zou, Y., Brebion, F. J. Org. Chem. (2006) [Pubmed]
  23. 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. Crich, D., Vinod, A.U. J. Org. Chem. (2005) [Pubmed]
  24. Synthesis of a 4,6-disubstituted dibenzofuran beta-sheet initiator by reductive radical arylation of benzene. Crich, D., Grant, D. J. Org. Chem. (2005) [Pubmed]
  25. Synthesis and stereoselective glycosylation of D- and L-glycero-beta-D-manno-heptopyranoses. Crich, D., Banerjee, A. Org. Lett. (2005) [Pubmed]
  26. Catalytic oxidation adjacent to carbonyl groups and at benzylic positions with a fluorous seleninic acid in the presence of iodoxybenzene. Crich, D., Zou, Y. J. Org. Chem. (2005) [Pubmed]
  27. 2-O-propargyl ethers: readily cleavable, minimally intrusive protecting groups for beta-mannosyl donors. Crich, D., Jayalath, P. Org. Lett. (2005) [Pubmed]
  28. Stereochemical memory effects in alkene radical cation/anion contact ion pairs: effect of substituents, and models for diastereoselectivity. Crich, D., Ranganathan, K. J. Am. Chem. Soc. (2005) [Pubmed]
  29. Facile dearomatizing radical arylation of furan and thiophene. Crich, D., Patel, M. Org. Lett. (2005) [Pubmed]
  30. 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. Crich, D., Jayalath, P. J. Org. Chem. (2005) [Pubmed]
  31. Is there a homolytic substitution chemistry (SH2) of sulfones?. Crich, D., Hutton, T.K., Ranganathan, K. J. Org. Chem. (2005) [Pubmed]
  32. Catalytic allylic oxidation with a recyclable, fluorous seleninic acid. Crich, D., Zou, Y. Org. Lett. (2004) [Pubmed]
  33. 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 synthesis of alpha-D-Gal-(1-->3)-alpha-D-Rha-(1-->3)- beta-D-Rha-(1-->4)-beta-D-Glu-OMe, the repeating unit of the antigenic lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652. Crich, D., Yao, Q. J. Am. Chem. Soc. (2004) [Pubmed]
  34. Mechanism of 4,6-O-benzylidene-directed beta-mannosylation as determined by alpha-deuterium kinetic isotope effects. Crich, D., Chandrasekera, N.S. Angew. Chem. Int. Ed. Engl. (2004) [Pubmed]
  35. 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. Crich, D., Li, W., Li, H. J. Am. Chem. Soc. (2004) [Pubmed]
  36. Direct synthesis of the beta-l-rhamnopyranosides. Crich, D., Picione, J. Org. Lett. (2003) [Pubmed]
  37. Asymmetric synthesis of highly substituted beta-nitro alcohols and enantiomerically enriched 4,4,5-trisubstituted oxazolidinones. Crich, D., Ranganathan, K., Rumthao, S., Shirai, M. J. Org. Chem. (2003) [Pubmed]
  38. Oxazolidinone protection of N-acetylglucosamine confers high reactivity on the 4-hydroxy group in glycosylation. Crich, D., Vinod, A.U. Org. Lett. (2003) [Pubmed]
  39. 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. Crich, D., Yao, Q. Org. Lett. (2003) [Pubmed]
  40. Tandem polar/radical crossover sequences for the formation of fused and bridged bicyclic nitrogen heterocycles involving radical ionic chain reactions, and alkene radical cation intermediates, performed under reducing conditions: scope and limitations. Crich, D., Ranganathan, K., Neelamkavil, S., Huang, X. J. Am. Chem. Soc. (2003) [Pubmed]
  41. Enantioselective cyclization of alkene radical cations. Crich, D., Shirai, M., Rumthao, S. Org. Lett. (2003) [Pubmed]
  42. 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/trimethylsilyl triflate. Crich, D., de la Mora, M., Vinod, A.U. J. Org. Chem. (2003) [Pubmed]
  43. 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. Crich, D., Vinod, A.U., Picione, J. J. Org. Chem. (2003) [Pubmed]
  44. Radical contraction of 1,3,2-dioxaphosphepanes to 1,3,2-dioxaphosphorinanes: a kinetic and (17)O NMR spectroscopic study. Crich, D., Sartillo-Piscil, F., Quintero-Cortes, L., Wink, D.J. J. Org. Chem. (2002) [Pubmed]
  45. Stereoselective formation of glycosyl sulfoxides and their subsequent equilibration: ring inversion of an alpha-xylopyranosyl sulfoxide dependent on the configuration at sulfur. Crich, D., Mataka, J., Zakharov, L.N., Rheingold, A.L., Wink, D.J. J. Am. Chem. Soc. (2002) [Pubmed]
  46. 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. Crich, D., Li, H. J. Org. Chem. (2002) [Pubmed]
  47. Generation and trapping of alkene radical cations under nonoxidizing conditions: formation of six-membered rings by exo- and endo-mode cyclizations. Crich, D., Neelamkavil, S. Org. Lett. (2002) [Pubmed]
  48. Solid-phase synthesis of beta-mannosides. Crich, D., Smith, M. J. Am. Chem. Soc. (2002) [Pubmed]
  49. Diastereoselectivity in the cyclization of alkene radical cations generated under non-oxidizing conditions: contact ion pairs and memory effects. Crich, D., Ranganathan, K. J. Am. Chem. Soc. (2002) [Pubmed]
  50. Fluorous dimethyl sulfide: a convenient, odorless, recyclable borane carrier. Crich, D., Neelamkavil, S. Org. Lett. (2002) [Pubmed]
  51. Generation and reaction of alkene radical cations under nonoxidizing conditions: synthesis of the pyrrolizidine nucleus. Crich, D., Ranganathan, K., Huang, X. Org. Lett. (2001) [Pubmed]
  52. Efficient one-pot conversion of carbonyl compounds to their alpha,beta-unsaturated derivatives using a recoverable, minimally fluorous organoselenium reagent. Crich, D., Barba, G.R. Org. Lett. (2000) [Pubmed]
  53. Efficient, diastereoselective chemical synthesis of a beta-mannopyranosyl phosphoisoprenoid. Crich, D., Dudkin, V. Org. Lett. (2000) [Pubmed]
  54. S-(4-methoxyphenyl) benzenethiosulfinate (MPBT)/trifluoromethanesulfonic anhydride: a convenient system for the generation of glycosyl triflates from thioglycosides. Crich, D., Smith, M. Org. Lett. (2000) [Pubmed]
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