An efficient stereoselective synthesis of enantiomerically pure aziridine derivatives of allyl β- d-glucopyranosides asymmetrically induced by a glucide moiety

Abstract

The enantiomerically pure title aziridines were obtained by regioselective azidolysis of the 2′,3′-epoxy derivatives of allyl 3,4,6-tri- O-benzyl-β- d-glucopyranosides, followed by cyclization of the corresponding azido alcohols by means of the PPh 3 protocol. Enantiomerically pure starting epoxides were prepared by epoxidation of the corresponding allyl 3,4,6-tri- O-benzyl-β- d-glucopyranosides asymmetrically induced by a glucide moiety.