SUGAR CHEMISTRY WITHOUT PROTECTING GROUPS: A NOVEL REGIOSELECTIVE SYNTHESIS OF 6-O-ACYL-D-GLUCOPYRANOSES AND METHYL-6-O-ACYL-α-D-GLUCOPYRANOSIDES

Article abstract of DOI:10.1016/S0040-4039(00)96390-1

The primary hydroxyl groups of α-D-glucose and methyl-α-D-glucoside were selectively esterified by treating the free sugars with N-acylthiazolidine-2-thiones, thus affording respectively 6-O-acyl-D-glucopyranoses and methyl-6-O-acyl-α-D-glucopyranosides in high yields.This new reaction is compared with our previous synthesis of 1-O-acyl-β-D-glucopyranoses from β-D-glucose and interpreted in terms of anomeric effect.