Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-chloro-2-(2-oxo-propyl)-purin-9-yl]-tetrahydro-furan-3-yl ester | 847829-95-2

• 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-(2-oxo-propyl)-purin-9-yl]-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[6-chloro-2-(2-oxopropyl)purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 847829-95-2
• 化学式: C₁₉H₂₁ClN₄O₈
• 分子量: 468.851
• InChiKey: TZEFFEMUYJJGAS-BGIGGGFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  11

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-(2-oxo-propyl)-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 1-[6-Chloro-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-propan-2-one
  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：

  乙酸异丙烯酯 、 2',3',5'-三-O-乙酰-6-氯-2-碘嘌呤核苷 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以85%的产率得到Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-chloro-2-(2-oxo-propyl)-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