Abstract
Treatment of methyl 4- O-benzoyl-2,3- O-isopropylidene-α- l-rhamnopyranoside and methyl 5- O-benzoyl-2,3- O-isopropylidene-α- d-lyxofuranoside with dibromomethyl methyl ether gave 2-bromo-2-deoxy-3- O-formylglycosyl bromides in good yields. Methyl 4,6-di- O-benzoyl-2,3- O-isopropylidene-α- O-mannopyranoside yielded a 6-bromo-6-deoxy-2- O-formylidose derivative via acyloxonium-ion rearrangements. Methyl 5- O-benzoyl-2,3- O-isopropylidene-β- d-ribofuranoside gave mainly a 2-bromo-2-deoxy derivative, but a small proportion of a 5-bromo-5-deoxy derivative could also be isolated. The glycosyl bromides were converted into the corresponding methyl glycosides. The O-formyl groups could be removed selectively.
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