INTRODUCTION OF C-SULFONATE GROUPS INTO DISACCHARIDE DERIVATIVES

To prepare C-sulfonate derivatives of disaccharides two different stra tegies were followed. Thus 6- and 6'-C-sulfocellobiosides 4 and 10-12 were prepared starting from a suitably protected cellobioside. The 6'- C-sulfoaminocellobioside 18 was prepared by construction of the molecu le through a glycosylation reaction. In both cases, the synthetic path way involves regioselective tosylation, introduction of a sulfur atom by nucleophilic displacement with potassium thioacetate and oxidation with hydrogen peroxide.