Preparation of Some Benzyl D-Glucuronatesfrom 4-Methoxybenzylidene Derivatives of D-Glucuronic Acid

Summary.  Because of the low stability of the benzyl ester linkage in benzyl 1,2:3,5-di-O-benzylidene-α-D-glucofuranuronate during the removal of the benzylidene groups by acid hydrolysis and/or hydrogenolysis, 4-methoxybenzylidene groups were used to block the free hydroxyl groups of D-glucuronic acid. Several benzyl esters of D-glucuronic acid were prepared, and their relative rates of acid catalyzed hydrolysis were determined by liquid-chromatographic separation of the reaction mixture and subsequent diode array detection. Received May 22, 2000. Accepted (revised) July 17, 2000