COMMERCIAL SYNTHESIS OF ALPHA-D-CELLOBIOSYL BROMIDE HEPTAACETATE

A detailed commercial process for the synthesis and purification of th e activated disaccharide, alpha-D-cellobiosyl bromide heptaacetate (1) was developed. Reaction Of alpha-D-cellobiose octaacetate (CBO) with HBr in glacial acetic acid or in glacial acetic acid/methylene chlorid e combination affords alpha-D-cellobiosyl bromide heptaacetate in high yield and excellent quality. Process variables such as reaction solve nt, reaction time, reaction temperature, HBr stoichiometry, isolation methods and product purification options were optimized for large-scal e synthesis. Alpha-D-cellobiosyl bromide heptaacetate was successfully prepared in a commercial manufacturing plant.