PREPARATION OF SUGAR PHOSPHATES BY DISPLACEMENT OF PRIMARY SULFONYLOXY GROUPS

A primary p-tolylsulfonyl group in certain otherwise acetylated sugars and glycosides can be displaced by diphenyl phosphate ion in refluxing dimethylformamide. Subsequent removal of protecting groups gives the phosphorylated sugar or glycoside. In this way D-glucose 6-phosphate was prepared in low yield and the anomeric methyl α- and β-D-glucopyranoside 6-phosphates in moderate yield (about 35%). In the last-mentioned case, methyl β-D-glucopyranoside 6-(monophenyl phosphate) was isolated as an intermediate. © 1968, American Chemical Society. All rights reserved.