Chem. Pharm. Bull. 50(11) 1453—1459 (2002)

and cheap and valuable sources of renewable materials for industrial applications. For example, sucrose can be converted to ethanol, which is widely used in various fields of industry and the source of C1 chemistry. Recently, natural disaccharides and trisaccharides have attracted enormous attention. A large number of oligosaccharides have been conjugated for new DNA-binding antitumor agents, and specific ligands for cell-surface recognition have been produced by chemical and enzymatic syntheses. We demonstrated that the reaction of D-glucose with cyclotriphosphate (P3m) afforded b-D-glucopyranosyl 1-triphosphate in good yield in a one-step process without protection of hydroxyl groups. Although D-glucose exists as an equilibrium mixture of a and b anomers under the reaction conditions, only b-D-glucopyranosyl 1-triphosphate was obtained stereoselectively. This method would be applicable to the phosphorylation of other monosaccharides. The phosphorylated products of oligoand polysaccharides are expected to act as chiral selectors, masking agents of metal ions, and material for drug delivery systems (DDS). Although this stereoselective phosphorylation is effective for monosaccharides, the existence of 1-OH is essential, which is not feasible in polysaccharides. It is more significant to apply this stereoselective phosphorylation reaction to disaccharides to open the way for the phoshorylation of oligoand polysaccharides. In the present study, the reaction of cellobiose (1), lactose (2), maltose (3), sucrose (4), and a ,a-trehalose (5) with P3m was studied to develop selective phosphorylation of disaccharides in aqueous solution.