Catalytic and Stereoselective Glycosylation with a Novel and Efficient Disarmed Glycosyl Donor: Glycosyl p-Trifluoromethylbenzylthio-p-trifluoromethylphenyl Formimidate

Abstract

Abstract A novel and efficient glycosyl donor having a p-trifluoro-methylbenzylthio-p-trifluoromethylphenyl formimidate function as a leaving group is easily prepared by the addition of anomeric hydroxyl group of 2,3,4,6-tetra-O-benzoyl-α,β-D-glucopyranose to p-trifluoromethylphenyl isothiocyanate, followed by treatment with p-trifluoromethylbenzyl bromide. Catalytic and stereoselective glycosylation using this glycosyl donor effectively proceeds by activating its nitorogen atom with various protic and Lewis acids.