Phosphorylation of D-Glucose Derivatives with Inorganic Cyclo-Triphosphate : Substituent Effect at the 5-CH₂OH or 2-OH Group

Abstract

The phosphorylation of several D-glucose derivatives has been achieved using inorganic sodium cyclotriphosphate hexahydrate (P_3m), Na₃P₃O₉·6H₂O, in aqueous solution. In the phosphorylation of D-glucuronic acid, 6-phosphoryl-D-glucose and D-xylose, β-D-glucuronic and 1-triphosphate, 6-phosphoryl-β-D-glucose 1-triphosphate and β-D-xylose 1-triphosphate were synthesized stereoselectively with maximum yields of 43.5, 32.8 and 41.9% respectively. In the case of D-glucosamine and 2-deoxy-D-glucose, the main phosphorylated products were assigned to β-D-glucosamine 1-triphosphate and 2-deoxy-β-D-glucose 1-triphosphate by ¹H-, ¹³C- and ³¹P-NMR, and the yields were 13.9 and 13.4%, respectively.