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Commercial synthesis of α-D-cellobiosyl bromide heptaacetate
Authors:Katherine D Goggin  Philip D Hammen  Kimberlee L Kuntson  Jack F Lambert  Stanley W Walinsky  Harry A Watson
Abstract:A detailed commercial process for the synthesis and purification of the activated disaccharide, α-D -cellobiosyl bromide heptaacetate ( 1 ) was developed. Reaction of α-D -cellobiose octaacetate (CBO) with HBr in glacial acetic acid or in glacial acetic acid/methylene chloride combination affords α-D -cellobiosyl bromide heptaacetate in high yield and excellent quality. Process variables such as reaction solvent, reaction time, reaction temperature, HBr stoichiometry, isolation methods and product purification options were optimized for large-scale synthesis. α-D -Cellobiosyl bromide heptaacetate was successfully prepared in a commercial manufacturing plant.
Keywords:α  -D-cellobiosyl bromide heptaacetate  acetobromo-α  -D-cellobiose  HBr bromination of α  -cellobiose octaacetate
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