Dj. Collins et Ed. Jones, REGIOSELECTIVE 2,3-DI-O-SILYLATION OF METHYL 6-CHLORO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE, Australian Journal of Chemistry, 47(7), 1994, pp. 1419-1421
Reaction of methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside (1) with a
n excess of t-butyldimethylsiyl chloride in dimethylformamide in the p
resence of imidazole gave 53% of the corresponding 2,3-di-O-t-butyldim
ethylsilyl ether (2); under similar conditions D-gluconic acid 1,5-lac
tone (3) afforded 83% of the 2,3,4,6-tetra-O-t-butyldimethylsilyl ethe
r (4).