Some observations on the synthesis of sophorose

Abstract

Condensation of tetra- O-acetyl-α- D-glucopyranosyl bromide with 1,3,4,6-tetra- O-acetyl-α- D-glucopyranose in acetonitrile solution containing mercuric cyanide and mercuric bromide affords the octa-acetates of both kojibiose (2- O-α- D-glucopyranosyl- D-glucose) and sophorose (2- O-β- D-glucopyranosyl- D-glucose). Each of these products can be isolated in approximately 28% yield. Although this method results in a lower over-all yield of sophorose from D-glucose than an alternative procedure, it has the advantage of being more rapid and direct, and is particularly well-suited to preparation of the acetylated glycosyl bromide.