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- W2013815330 abstract "Abstract Selective benzoylation of 1,6-anhydro-4′,6′- O -benzylidene-β-lactose ( 1 ), using 2.1 molar equivalents of benzoyl chloride in pyridine at — 20°, yielded five benzoates which were designated 2 to 6 in order of decreasing R F value on t.l.c. After column chromatography on silica gel, compounds 2 – 6 were separated as the 2,2′,3,3′-tetra-benzoate ( 2 , 3%), 2,3,3′-tribenzoate ( 3 , 11%), 2,2′,3′-tribenzoate ( 4 , 5%), 2,3′-dibenzoate ( 5 , 30%), and 3′-benzoate ( 6 , 22%), respectively. Selective benzoylation of 5 , using 1.1 molar equivalents of benzoyl chloride, afforded 2 , 3 , and 4 in yields of 15, 56, and 8%, respectively, together with 5% of 5 . Thus, the order of reactivities of the secondary hydroxyl groups in 1 is 3′>3>2′. Compounds 3 – 6 have potential value in the chemical modification of lactose or the synthesis of lactose-containing oligosaccharides." @default.
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- W2013815330 date "1975-12-01" @default.
- W2013815330 modified "2023-09-27" @default.
- W2013815330 title "Studies on the reactivities of the secondary hydroxyl groups in 1,6-anhydro-4′,6′-o-benzylidene-β-lactose by selective benzoylation" @default.
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- W2013815330 doi "https://doi.org/10.1016/s0008-6215(00)85861-9" @default.
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