Hydrogen peroxide oxidation of palatinose and trehalulose:: direct preparation of carboxymethyl α-D-glucopyranoside

The direct oxidation of palatinose and trehalulose by hydrogen peroxide in acidic medium provided carboxymethyl alpha -D-glucopyranoside (alpha -CMG) in moderate to fair yields in a single step. The effect of catalytic sodium tungstate on the reaction was studied. alpha -CMG is a versatile synthon able to supply a glucosyl moiety through the acylation of alcohols or amines, via the opening of the delta -lactone obtained by acetylation. (C) 2000 Elsevier Science Ltd. All rights reserved.