Donald L. MacDonald

PHOSPHATE ESTERS: Glycosyl Phosphates

Publisher Summary This chapter discusses the formation of a glycosyl phosphate. The preparation of glycosyl phosphates involves the direct fusion at moderate temperatures of fully acetylated sugars with anhydrous phosphoric acid. This procedure, thus, not only obviates the preparation of acetylated glycosyl halides but also circumvents the need to prepare salts of phosphoric acid or its diesters. The method appears to be of general applicability and has been used for the preparation of glycosyl phosphates of a number of different types of sugar such as aldoses, ketohexoses, amino sugars, methyl pentoses, and disaccharides. This formation of a glycosyl phosphate by replacement of an acetoxy group on C-1 of, for example, β - d -glucopyranose pentaacetate, where the acetoxy groups on C-1 and C-2 are in a trans relationship, proceeds presumably via a cyclic ion and the first product formed should be a derivative of β - d -glucopyranosyl phosphate.