Journal
CARBOHYDRATE RESEARCH
Volume 343, Issue 8, Pages 1297-1308Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2008.03.019
Keywords
glycosylation; disarmed glycosyl halides; Lewis acids; NBS; anomer
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Reactions of O-benzoylated glucopyranosyl halide (I, Br), isolated or generated in situ from per-benzoylated glucose (8a) and trimethylsilyl halide, with various alcohols were efficiently promoted by zinc halide (Cl, Br) or N-bromosuccinimide with a catalytic ZnI2 to give the corresponding 1,2- trans-beta-glucosides in good to high yields. When the anomeric halogenation of 8a was carried out in the presence of reactive alcohols, 1,2-cis-alpha-glucosides were selectively formed. (C) 2008 Elsevier Ltd. All rights reserved.
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