REACTION OF O-BENZYLIDENE SUGARS WITH N-BROMOSUCCINIMIDE .2. SCOPE AND SYNTHETIC UTILITY IN METHYL 4,6-O-BENZYLIDENEHEXOPYRANOSIDE SERIES

Treatment of methyl 4,6-O-benzylidenehexopyranosides with N-bromosuccinimide in refluxing carbon tetrachloride or a suitable chlorinated hydrocarbon affords with few exceptions methyl 4-O-benzoyl-6-bromo-6-deoxyhexopyranosides as the preponderant products. Many of the groups utilized in the protection of hydroxyl groups are unaffected by the reaction conditions. Anhydro rings also remain intact. The reaction provides a convenient route to selectively C-4 benzoylated 6-substituted hexopyranose derivatives which are amenable to a variety of transformations and can serve as intermediates to 6-deoxy, 6-amino, etc. hexoses. © 1969, American Chemical Society. All rights reserved.