Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-chloro-2-prop-2-ynyl-purin-9-yl)-tetrahydro-furan-3-yl ester | 847829-98-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-chloro-2-prop-2-ynyl-purin-9-yl)-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-chloro-2-prop-2-ynylpurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 847829-98-5
• 化学式: C₁₉H₁₉ClN₄O₇
• 分子量: 450.835
• InChiKey: IUEXWACUYIBLSK-BGIGGGFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-chloro-2-prop-2-ynyl-purin-9-yl)-tetrahydro-furan-3-yl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (2R,3R,4S,5R)-2-(6-Chloro-2-prop-2-ynyl-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Facile, chemoenzymatic synthesis of the potent antiviral compound, 2-acetonylinosine

  摘要：

  A facile and efficient methodology for the chemoenzymatic synthesis of the antiviral compound, 2-acetonylinosine has been developed. The present synthetic strategy, which has generality, is a dramatic improvement on the methodologies currently available for the synthesis of functionalized purine nucleosides of therapeutic interest. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.065
• 作为产物：
  描述：

  2,3,5-三-O-乙酰基-6-氯嘌呤-9-β-D-呋喃核糖苷 、 3-溴丙炔 在 三丁基氯化锡 、 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-chloro-2-prop-2-ynyl-purin-9-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Facile, chemoenzymatic synthesis of the potent antiviral compound, 2-acetonylinosine

  摘要：

  A facile and efficient methodology for the chemoenzymatic synthesis of the antiviral compound, 2-acetonylinosine has been developed. The present synthetic strategy, which has generality, is a dramatic improvement on the methodologies currently available for the synthesis of functionalized purine nucleosides of therapeutic interest. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.065