Selective Benzoylation of Methyl 6-Deoxy-α- and β-D-glucopyranosides

Selective dimolar benzoylation of methyl 6-deoxy-α- and β- D -glucopyranosides yielded the 2,3-di-O-benzoate of the respective glucopyranoside as the major product in 61 and 29% yields. The orders of the reactivity of the secondary hydroxyl groups in α- and β-anomers were different, i.e., the order...

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Bibliographic Details
Published in:Canadian journal of chemistry 1973-10, Vol.51 (19), p.3272-3276
Main Authors: Kondo, Yôtaro, Miyahara, Kiyoshi, Kashimura, Naoki
Format: Article
Language:English
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Summary:Selective dimolar benzoylation of methyl 6-deoxy-α- and β- D -glucopyranosides yielded the 2,3-di-O-benzoate of the respective glucopyranoside as the major product in 61 and 29% yields. The orders of the reactivity of the secondary hydroxyl groups in α- and β-anomers were different, i.e., the order was 2-OH > 3-OH > 4-OH for the former and 3-OH > 2-OH > 4-OH for the latter.
ISSN:0008-4042
1480-3291
DOI:10.1139/v73-488