Study of the stereoselectivity of 2-azido-2-deoxyglucosyl donors: protecting group effects

Abstract

A series of tolyl 2-azido-2-deoxy-thio-glucoside donors with different combinations of protecting groups were prepared. These donors were used in glycosylation reactions to test the correlations between the stereoselectivity and the pattern of the protecting groups. Acetyl groups showed a position dependent stereo-directing effect. A remote participating mechanism is proposed to explain the observed results.