Regioselective Control in the Oxidative Cleavage of 4,6-O-Benzylidene Acetals of Glycopyranosides by Dimethyldioxirane

The oxidative cleavage of 4,6-O-benzylidene acetals of glycopyranosides using dimethyldioxirane (DMDO) leads to the corresponding hydroxy-benzoates in excellent yields. With a proper choice of the neighboring protecting groups, this oxidative fragmentation provides the 6- or 4-hydroxyl derivatives in a highly regioselective manner.