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Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Selective Methanolysis of Lactone Rings in Some Acyl Carbohydrates
ISAO MATSUNAGAZENZO TAMURA Faculty of Pharmaceutical Sciences, University of Tokyo">
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JOURNAL FREE ACCESS

1969 Volume 17 Issue 7 Pages 1383-1389

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Abstract

It was found that a lactone ring was esterified to a methyl ester group in the bufferized methanol containing triethylamine-acetic acid or sodium acetate without simultaneous cleavage of the acyl groups and the methyl ester groups and this methanolysis mainly proceeded without acyl migration. Using this method, 2, 4-O-benzylidene-5-O-acyl-D-glucaro-6, 3-lactone 1-methyl esters (II, III, IV and V) were esterified in excellent yields to dimethyl 2, 4-O-benzylidene-5-O-acyl-D-glucarates (VII, VIII, IX and X respectively), and from the latters, dimethyl 2, 4-O-benzylidene-3-O-acetyl-5-O-acyl-D-glucarates (XI, XII, XIII and XIV respectively) were synthesized by the usual acetylation. Moreover, 1, 2-O-isopropylidene-5-O-acetyl-D-glucofuranurono-6, 3-lactone (XIX) could be also esterified to methyl 1, 2-O-isopropylidene-5-O-acetyl-D-glucofuranuronate (XX) by the same method.

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© The Pharmaceutical Society of Japan
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