A General Method Based on the Use of<i>N</i>-Bromosuccinimide for Removal of the Thiophenyl Group at the Anomeric Position to Generate A Reducing Sugar with the Original Protecting Groups Still Present

Abstract

Abstract Efficient conversion of a range of different phenyl thioglycosides into their hemiacetals has been achieved by treatment with N-bromosuccinimide in aqueous acetone. The method is mild and general since it does not interfere with the presence of other protecting groups like acetate, benzyl, benzylidene acetal, tert-butyldiphenylsilyl groups, and the O-glycosidic bond (e.g. di-, tetra-, and pentasaccharide thioglycosides).