Recent advances in glycosylation reactions

Abstract

Secondary amides react smoothly with benzylated glycosyl chlorides in the presence of a silver salt to give a new class of imidates which can be used in a novel method of a-glycoside synthesis. A practical and stereospecific approach to a variety of a-0-glucosides, a-0-galactosides, and a-L-fucosides is thereby provided. Applications of the method in the synthesis of several human blood group antigenic determinants is described together with other synthetic uses of sugar imidates.