Regioselective Syntheses of Mono-O-acylglucoses

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概要

• 論文の詳細を見る

• All isomeric 1α-, 1β-, 2-, 3-, 4-, and 6-mono-O-acyl-D-glucopyranoses (acyl group from caprinoyl through stearoyl) were synthesized in a regio-(and stereo-) selective manner. Gas-liquid chromatography (trimethylsilyl (TMS) derivatives), infrared, and ^1H-nuclear magnetic resonance data, which provided evidence for assignment of the position of the acyl chain, are described. Compounds previously reported to be 2-O-acyl and 3-O-acyl-D-glucoses were shown to be 6-O-acyl derivatives. In the 3-and 6-O-acyl derivatives, anomerization was slow and they were present largely as α-anomers, while the 2-and 4-O-acyl derivatives were mixtures of α-and β-anomers due to their rapid anomerization. Some di-O-acyl-D-glucopyranoses (1β, 6-, 2,3-, and 4,6-) and a new tri-O-acyl-D-glucopyranose (2,4,6-) were also prepared, all of them except for the 1β, 6-di-O-acyl derivative were obtained as α-anomers.

• 社団法人日本薬学会の論文
• 1979-11-25

著者

• 津田 喜典

  金沢大学

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 西川 嘉廣

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 津田 喜典

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 吉本 公浩

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 吉本 公浩

  金沢大学薬学部

• 佐々木 和美

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 田原 計子

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 鈴木 重通

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 西川 嘉廣

  金沢大学薬学部

• 西川 嘉廣

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 鈴木 重通

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 田原 計子

  Faculty Of Pharmaceutical Sciences Kanazawa University

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