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.
Stévenin
Arnaud
A
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 avenue de la Terrasse, F-91198 Gif-sur-Yvette Cedex, France.
Boyer
François-Didier
FD
Beau
Jean-Marie
JM