Regioselective enzymic deacetylation of octa-O-acetylsucrose: preparation of hepta-O-acetylsucroses.

Deacetylation of octa-O-acetylsucrose (1) with Alcalase or protease N gave the 2,3,4,6,3',4',6'-hepta-acetate (2) as the initial major product with the 2,3,4,6,3',4'-hexa-acetate (3) as the subsequent main product. The 2,3,4,1',3',4',6'-hepta-acetate (5) was obtained from 1 by the action of lipase OF or lipase AP6, and the 2,3,4,6,1',3',6'-(4) and 2,3,4,6,1',3',4'-hepta-acetate (7) by the action of Candida lipase and chymotrypsin, respectively. The 2,3,6,1',3',4',6'-hepta-acetate (6) was formed from 5 by acyl migration.