Facile cleavage of carbohydrate benzyl ethers and benzylidene acetals using the [formula omitted] reagent under two-phase conditions

Abstract

Benzyl ether and benzylidene acetal carbohydrate protecting groups can be selectively cleaved by reaction with sodium bromate/sodium dithionite in ethyl acetate/water. Under the mild (room temperature, short reaction time) conditions needed, a variety of other protecting functionalities such as acetyl, chloroacetyl, benzoyl, pivaloyl, tosyl, t-butyldimethylsilyl, trityl, and isopropylidene groups remain unaffected.