Selective Monoesterification of Unprotected Mono and Disaccharides

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Abstract
Under mild conditions, treatment of unprotected methyl-α-D-glucopyranoside, N-acetylglucosamine and maltose with triphenylphosphine, diethylazodicarboxylate and equimolar amount of various carboxylic acids allowed regioselective 6-O-esterifications (6′-O for maltose) of the carbohydrate without esterification of other hydroxyl groups. This reaction found an application in the synthesis of liposoluble, labelled sugars and hydrosoluble polymers.