The reaction of O-benzylidene sugars with N-bromosuccinimide
作者： Stephen Hanessian
DOI: 10.1016/S0008-6215(00)81783-8
关键词: Halogenation 、 N-Bromosuccinimide 、 Protonation 、 Acetal 、 Ring (chemistry) 、 Chemistry 、 Stereoselectivity 、 Ion 、 Medicinal chemistry 、 BENZOXONIUM
摘要: The reaction of 2',3'-0-benzylideneuridine with N-bromosuccinimide (NBS) leads to 3'-0-benzoyl-2',5dibromouridine. stereoselectivity bromination in the sugar ring can be explained by invoking sequential formation benzoxonium ion and 2,2'-anhydronucleoside intermediates. Protonation appropriate 2,2'-anhydronucleoside, followed treatment NBS, recreates conditions which prevail original benzylidene acetal NBS.
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