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 α-d-glucopyranoside (α-CMG) in moderate to fair yields in a single step. The effect of catalytic sodium tungstate on the reaction was studied. α-CMG is a versatile synthon able to supply a glucosyl moiety through the acylation of alcohols or amines, via the opening of the δ-lactone obtained by acetylation.