Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Chemistry of Oxo-Sugars. (2). Regio- and Stereo-Selective Synthesis of Methyl D-Hexopyranosiduloses and Identification of Their Forms Existing in Solutions
Hong-Min LIUYoshiyuki SATOYoshisuke TSUDA
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1993 Volume 41 Issue 3 Pages 491-501

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Abstract

Sixteen oxo derivatives of methyl D-hexopyranosides with various regio- and stereo-chemistries were selectively synthesized by direct oxidation of non-protected methyl glycosides by the bistributyltin oxide-bromine method or by oxidation of pfrtially protected glycosides followed by deprotection. The forms of these oxoglycosides existing in pryidine-d5 and in H2O (D2O) were investigated by means of 13C-NMR spectroscopy, and it was found that interconversion between oxo and hydrate forms of oxoglycosides readily takes place.

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© The Pharmaceutical Society of Japan
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