N-Bromosuccinimide-Mediated Conversion of Allyl Glycosides to Glycosyl Hemiacetals

Abstract

A novel reaction condition has been developed for the hydrolysis of differentially functionalized allyl glycosides to their corresponding glycosyl hemiacetal derivatives in the presence of N-bromosuccinimide (NBS). The reaction condition is exceptionally fast, mild, and compatible with most of the functional groups used in the oligosaccharide synthesis, and yields were excellent.