Commercial synthesis of alpha-D-cellobiosyl bromide heptaacetate.
A detailed commercial process for the synthesis and purification of the 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 chloride combination affords alpha-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. alpha-D-Cellobiosyl bromide heptaacetate was successfully prepared in a commercial manufacturing plant.
Goggin
K D
KD
Central Research Division, Pfizer Inc., Groton, Connecticut 06340.
Hammen
P D
PD
Knutson
K L
KL
Lambert
J F
JF
Walinsky
S W
SW
Watson
H A
HA
D000085:Acetates / Q000138:chemical synthesis* / Q000302:isolation & purification; D002240:Carbohydrate Sequence; D002475:Cellobiose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002851:Chromatography, High Pressure Liquid; D004187:Disaccharides / Q000138:chemical synthesis* / Q000302:isolation & purification; D005374:Filtration; D018054:Hydrobromic Acid; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure
D000085:Acetates; D004187:Disaccharides; C088313:cellobiosyl bromide heptaacetate; D002475:Cellobiose; D018054:Hydrobromic Acid