Synthesis of Tetrazolyl Derivatives of 3-Deoxy-D-glycero-D-galacto-2-onulosonic Acid (KDN) as Useful Glycosyl Donors, and Their Application for O- and C-Glycosylations

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概要

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• The reaction of methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-D-galacto-2-nonulopyranosonate (3) with S, S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate (4) gave methyl (1-phenyl-1H-tetrazol-5-yl 4,5,7,8,9-tetra-O-acetyl-3-deoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate (5) and methyl (1-phenyl-5-thioxo-1H, 4H-tetrazol-4-yl4,5,7,8,9-penta-O-acetyl-2,3-dideoxy-D-glycero-α- and -β-D-galacto-2-nonulopyranosid)onate (6,7). The structures were elucidated by means of ultraviolet (UV), circular dichroism (CD), and ^<13>C-nuclear magnetic resonance(^<13>C-NMR) spectral examination, and X-ray crystal analysis. These S- and N-glycosides were applied to O-glycosylation with suitable promoters, and when palladium (II) was used as a promoter, glycosylation of 5 with 2-propanol gave the corresponding glycosides in good yield. Moreover. the S-glycoside was applied to C-glycosylations.

• 公益社団法人日本薬学会の論文
• 1993-01-15

著者

• 小倉 治夫

  School of Pharmaceutical Sciences, Kitasato University

• 高柳 弘明

  School of Pharmaceutical Sciences, Kitasato University

• 高柳 弘明

  北里大・薬

• 小倉 治夫

  北里大学

• 小倉 治夫

  School Of Pharmaceutical Sciences Kitasato University

• 中村 光延

  School of Pharmaceutical Sciences, Kitasato University

• 高柳 弘明

  北里大学薬学部薬化学教室

• 高柳 弘明

  School Of Pharmaceutical Sciences Kitasato University

• 武田 収功

  School of Pharmaceutical Sciences, Kitasato University

• 武田 収功

  School Of Pharmaceutical Sciences Kitasato University

• 浅井 紀枝

  School of Pharmaceutical Sciences, Kitasato University

• 井端 直子

  School of Pharmaceutical Sciences, Kitasato University

• 浅井 紀枝

  School Of Pharmaceutical Sciences Kitasato University

• 中村 光延

  School Of Pharmaceutical Sciences Kitasato University

• 井端 直子

  School Of Pharmaceutical Sciences Kitasato University

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