Syntheses and ^1H- and ^<13>C-Nuclear Magnetic Resonance Spectra of All Positional Isomers of Methyl Mono-O-tetradecanoyl-a- and β-D-Glucopyranosides
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概要
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All the isomers of the mono-O-myristoyl derivative of methyl α- and β-D-glucopyranosides were unambiguously prepared, and their ^1H- and ^<13>C-NMR spectra are discussed in relation to the stereochemistry of the pyranose ring and ester grouping. The acylation shifts on introducing a myristoyl group at each carbon atom of the pyranose ring in the acyl derivatives were tabulated and were shown to be additive parameters for diacyl derivatives. A diacyl mixture obtained by direct acylationof methyl β-D-glucopyranoside could be completely analyzed by ^<13>C-NMR. The effects of orientational differences of an anomeric methoxyl group on pyranose carbon shielding were also clarified in every mono-O-myristoyl-D-glucopyranoside. An anomalous effect at C^2 of the 2-O-acyl derivative is suggested to originate from a conformational change of the ester group in the β-anomer.
- 公益社団法人日本薬学会の論文
- 1980-01-25
著者
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津田 喜典
金沢大学
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津田 喜典
Faculty of Pharmaceutical Sciences, Kanazawa University
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板谷 芳京
Faculty of Pharmaceutical Sciences, Kanazawa University
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津田 喜典
Faculty Of Pharmaceutical Sciences Kanazawa University
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吉本 公浩
Faculty of Pharmaceutical Sciences, Kanazawa University
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吉本 公浩
金沢大学薬学部
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板谷 芳京
金沢大学薬学部
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板谷 芳京
Faculty Of Pharmaceutical Sciences Kanazawa University
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柴田 かの子
Faculty of Pharmaceutical Sciences, Kanazawa University
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柴田 かの子
Faculty Of Pharmaceutical Sciences Kanazawa University
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