Glycosyl Glycerol Derivatives as Drug Carrier System. Stereoselective Synthesis of EpoxyalkylN-Acyl-β-D-glucopyranosides and Their Reactivity with Nucleophiles

Abstract

The synthesis of alkenyl 2-acylamino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosides from N-acetyl-D-glucosamine is described. The oxidation of alkenyl glycosides with m-CPBA gives the corresponding oxiranes in good yields, and with high stereoselectivity. Analogues of glycosyl glycerol derivatives, which can be used as drug carriers, were obtained by various ring-opening reactions with different nitrogen, sulfur, and carbon nucleophiles.