O-ethyl O'-[2,3-O-isopropylidene-1-(6-chloropurin-9-yl)-β-D-ribofuranosyl][(diethoxyphosphinyl)methyl]phosphonate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: O-ethyl O'-[2,3-O-isopropylidene-1-(6-chloropurin-9-yl)-β-D-ribofuranosyl][(diethoxyphosphinyl)methyl]phosphonate
• 英文别名: 9-[(3aR,4R,6R,6aR)-6-[[diethoxyphosphorylmethyl(ethoxy)phosphoryl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-chloropurine
• 化学式: C₂₀H₃₁ClN₄O₉P₂
• 分子量: 568.888
• InChiKey: JGPZMCIBOAGKFA-QJGNXNGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  甲基膦酸二乙酯 、 6-氯-9-beta-D-(2,3-异亚丙基)呋喃核糖基嘌呤 、 二氯磷酸乙酯 在 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.33h， 以80%的产率得到O-ethyl O'-[2,3-O-isopropylidene-1-(6-chloropurin-9-yl)-β-D-ribofuranosyl][(diethoxyphosphinyl)methyl]phosphonate
  参考文献：
  名称：

  Monoglycosyl, diglycosyl, and dinucleoside methylenediphosphonates: direct synthesis and antiviral activity

  摘要：

  A direct and general access to D-glycosyl 3-, 5-, or 6-methylenediphosphonates, di-D-glycosyl 1,5-, 3,5-, 3,6-, 5,5-, or 6,6-methylenediphosphonates and dithymidine 3',5'-methylenediphosphonate is described. The method involves the one-pot alkylidenediphosphorylation of glycosyl or thymidine derivatives. No antiviral activity was detected against a panel of RNA and DNA viruses. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.023

文献信息

• Monoglycosyl, diglycosyl, and dinucleoside methylenediphosphonates: direct synthesis and antiviral activity
  作者：Claude Grison、Stéphane Joliez、E. De Clercq、Philippe Coutrot

  DOI：10.1016/j.carres.2006.03.023

  日期：2006.7

  A direct and general access to D-glycosyl 3-, 5-, or 6-methylenediphosphonates, di-D-glycosyl 1,5-, 3,5-, 3,6-, 5,5-, or 6,6-methylenediphosphonates and dithymidine 3',5'-methylenediphosphonate is described. The method involves the one-pot alkylidenediphosphorylation of glycosyl or thymidine derivatives. No antiviral activity was detected against a panel of RNA and DNA viruses. (c) 2006 Elsevier Ltd. All rights reserved.