Chemistry Letters · 2002 · 24 citations · 11 references
Natural SciencesChemistryCarbohydrate ChemistryCatalysisOrganic ChemistryCatalytic MechanismsGlycosidic Bond FormationGlycosylation PathwaysChemical GlycosylationChemoselective CatalysisChemoselective SynthesisGlycoconjugate SynthesisGlycoside SynthesisGlycosylation CatalysisStereoselective GlycosylationStereoselective Synthesis
Abstract Catalytic and chemoselective glycosylation between novel “armed” and “disarmed” glycosyl p-trifluoromethylbenzylthio-p-trifluoromethylphenyl formimidates was effectively performed in the presence of a catalytic amount of TfOH and MS 4A in CH2Cl2 at -78 °C. In addition, it was noted that highly 1,2-cis or 1,2-trans stereoselective synthesis was established when the above glycosylation was carried out at -78 °C in tBuOMe or EtCN, respectively.
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G.H. Veeneman, Steven H. van Leeuwen, Jacques H. van Boom · Tetrahedron Letters · 1990 · 866 citations