Acid-catalysed hydrolysis of 1,2-O-alkylidene-α-D-glucofuranoses

Abstract

The rates of acid-catalysed hydrolysis of 1,2-O-alkylidene-alpha-D-glucofuranoses indicate that, for oligosaccharide synthesis, cyclopentylidene and cycloheptylidene acetals are better protecting groups than the isopropylidene residue. Hydrolysis was impeded by a nitrate group at position 5 and more so by one at position 3. The hydrolyses were accompanied by a positive drift in optical rotation, except for the 5-O-substituted compounds where the formation of D-glucopyranose derivatives cannot occur.