A Mild and Environmentally Benign Synthetic Protocol for Catalytic Hydrolysis of Thioglycosides

Abstract

A wide variety of thioglycosides 1 are selectively hydrolyzed to the corresponding 1-hydroxy sugars 2 in good yields at 0-5 °C, by employing V 2 O 5 -H 2 O 2 catalyzed oxidation of ammonium bromide in CH 2 Cl 2 -H 2 O solvent system. The methodology is very mild, environmentally benign, efficient and highly chemoselective. No side reactions such as bromination either at the anomeric position or double bond or oxidation at the sulfur are encountered.