Citric acid mediated simple and stereoselective synthesis of o-linked glycosides by Ferrier rearrangement

Abstract

A simple and environment-friendly citric acid-mediated synthesis of glycosides has been reported using Ferrier-rearrangement. Using this protocol, synthesis of several glycosides including pseudo disaccharides was prepared. Citric acid was successfully employed for the synthesis of glycosides from D-glucal, L-rhamnal, D-xylal and D-galactal with various alcohols to give a broad range of glycosides in up to 80% yields with α-isomer as major product under mild reaction conditions.