Regioselective 2,3-Di-O-silylation of Methyl 6-Chloro-6-deoxy-α-D-glucopyranoside

Abstract

Reaction of methyl 6-chloro-6-deoxy-α-D-glucopyranoside (1) with an excess of t- butyldimethyl-silyl chloride in dimethylformamide in the presence of imidazole gave 53% of the corresponding 2,3-di-O-t-butyldimethylsilyl ether (2); under similar conditions D-gluconic acid 1,5-lactone (3) afforded 83% of the 2,3,4,6-tetra-O-t-butyldimethylsilyl ether (4).