Studies on Sialic Acids. XXV. Synthesis of the α- and β-N-Glycosides of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN)

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概要

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• Several α- and β-N-glycosides of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (1,KDN) were synthesized under Vorbruggen and Williamson reaction conditions. Two hexa-O-acetyl derivatives of 1 were treated with trimethylsilyl deriatives of pyrimidine, 5-fluoropyrimidine and 5-methylpyrimidine, and azidotrimethylsilane so give mixtures of α- and -β-N-glycoside derivatives of 1. Two penta-O-acetyl-2-chloro derivatives of 1 were treated with the sodium salts of 2,4(1H, 3H)-pyrimidinedione, 5-fluoro-2,4(1H, 3H)-pyrimidinedione and 5-methyl-2,4(1H, 3H)-pyimidinedione to give only the α-N-glycosides. THe anomeric configurations of these compounds could be elucidated on the basis of the coupling pattern of C-1 in ^<13>C-nuclear magnetic resonance spectral analysis.

• 社団法人日本薬学会の論文
• 1991-12-25

著者

• 古畑 公夫

  School of Pharmaceutical Sciences, Kitasato University

• 小倉 治夫

  School of Pharmaceutical Sciences, Kitasato University

• 古畑 公夫

  北里大薬

• 小倉 治夫

  北里大学

• 小倉 治夫

  School Of Pharmaceutical Sciences Kitasato University

• 山崎 聡子

  School Of Pharmaceutical Sciences Kitasato University

• 中村 光延

  School of Pharmaceutical Sciences, Kitasato University

• 中村 光延

  School Of Pharmaceutical Sciences Kitasato University

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