Abstract
Selective benzoylation of 1, 6-anhydro-4', 6'-O-benzylidene-β-maltose (1), using 2 molar equivalents of benzoyl chloride in pyridine at ca. -10°, yielded five benzoates which were designated 2 to 6 in order of decreasing Rf value on TLC. After column chromatography on silica gel, compounds 2 to 6 were separated as the 2, 2', 3, 3'-tetrabenzoate (2, 1.2%), 2, 2', 3'-tribenzoate (3, 2.8%), 2, 2'-dibenzoate (4, 9%), 2', 3'-dibenzoate (5, 7.3%), and 2'-benzoate (6, 48%), respectively. Thus, the order of reactivities of the secondary hydroxyl groups in 1 is 2'>2, 3'>3. Compound 3 to 6 have potential value in the chemical modification of maltose or the synthesis of maltose-containing oligosaccharides.
