Synthetic Studies on Glyceroglycolipids

Abstract

A regio- and stereo-controlled synthesis of a sulfated glyceroglycolipid 1 is described. A key glycosyl acceptor 3 was prepared in a regioselective way by use of a dibutylstannylene intermediate. A key glycosyl donor 2 was synthesized in a stereocontrolled way by use of allyl, benzyl, and monochloroacetyl groups as the protective groups for the D-glucosyl residue. The key glycosidation between 2 and 3 could be achieved in a stereoselective way in the presence of AgOSO₂CF₃ to give 26 with the desired stereochemistry. Further transformation of 26 into 1 could be performed via 28 obtained by a regioselective deprotection of the acyl groups.