(4S,5S,6S,7R)-4,5,6-Trihydroxy-7-hydroxymethyl-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylic acid methyl ester | 200810-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: (4S,5S,6S,7R)-4,5,6-Trihydroxy-7-hydroxymethyl-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylic acid methyl ester
• 英文别名: methyl (4S,5S,6S,7R)-4,5,6-trihydroxy-7-(hydroxymethyl)-4,5,6,7-tetrahydrotriazolo[1,5-a]pyridine-3-carboxylate
• CAS: 200810-11-3
• 化学式: C₉H₁₃N₃O₆
• 分子量: 259.219
• InChiKey: OCHMMCFONOAPCU-QAPAGQKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S,5S,6S,7R)-4,5,6-Trihydroxy-7-hydroxymethyl-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 反应 12.0h， 以97%的产率得到(4S,5S,6S,7R)-4,5,6-Trihydroxy-7-hydroxymethyl-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylic acid
  参考文献：
  名称：

  Triazole carboxylic acids as anionic sugar mimics? Inhibition of glycogen phosphorylase by a d-glucotriazole carboxylate

  摘要：

  Triazole-carboxylic acids related to D-glucose and D-galactose may be prepared by intramolecular [1,3]-dipolar cycloadditions of azides to unsaturated esters, followed by bromine oxidation of the resulting triazoline. Such materials may provide a series of anionic mimics of carbohydrates. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00561-2
• 作为产物：
  描述：

  2,3-di-O-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-glucono-1,4-lactone 在 吡啶 、 咪唑 、 甲醇 、 sodium azide 、 二异丁基氢化铝 、 氧化汞红 、 potassium carbonate 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 40.42h， 生成 (4S,5S,6S,7R)-4,5,6-Trihydroxy-7-hydroxymethyl-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Triazole carboxylic acids as anionic sugar mimics? Inhibition of glycogen phosphorylase by a d-glucotriazole carboxylate

  摘要：

  Triazole-carboxylic acids related to D-glucose and D-galactose may be prepared by intramolecular [1,3]-dipolar cycloadditions of azides to unsaturated esters, followed by bromine oxidation of the resulting triazoline. Such materials may provide a series of anionic mimics of carbohydrates. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00561-2

文献信息

• Triazole carboxylic acids as anionic sugar mimics? Inhibition of glycogen phosphorylase by a d-glucotriazole carboxylate
  作者：Thomas M. Krülle、Carmen de la Fuente、Lea Pickering、Robin T. Aplin、Katerina E. Tsitsanou、Spyros E. Zographos、Nikos G. Oikonomakos、Robert J. Nash、Rhodri C. Griffiths、George W.J. Fleet

  DOI：10.1016/s0957-4166(97)00561-2

  日期：1997.11

  Triazole-carboxylic acids related to D-glucose and D-galactose may be prepared by intramolecular [1,3]-dipolar cycloadditions of azides to unsaturated esters, followed by bromine oxidation of the resulting triazoline. Such materials may provide a series of anionic mimics of carbohydrates. (C) 1997 Elsevier Science Ltd.