(1S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(6-chloropurin-9-yl)-2,2-difluorocyclopentanol | 902118-90-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(6-chloropurin-9-yl)-2,2-difluorocyclopentanol
• CAS: 902118-90-5
• 化学式: C₂₆H₂₇ClF₂N₄O₂Si
• 分子量: 529.061
• InChiKey: BTETZMLARZEPEP-URVUXULASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  73.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(6-chloropurin-9-yl)-2,2-difluorocyclopentanol 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以81%的产率得到(1S,3S,5R)-5-(6-aminopurin-9-yl)-3-(tert-butyldiphenylsilanyloxy)-2,2-difluorocyclopentanol
  参考文献：
  名称：

  3′-Fluoro-3′-deoxy-5′-noraristeromycin derivatives: Synthesis and antiviral analysis

  摘要：

  The promising antiviral properties of 3'-fluoro-3'-deoxyadenosine and 4',4'-difluoro-4'-deoxy-5'-noraristeromycin prompted the synthesis of the corresponding 3'-fluoro derivatives of 5'-noraristeromycin. These target compounds, which were prepared from the same readily accessible cyclopentenol, were found to be inactive when subjected to 31 viral assays. The results have some implications on the mechanism of antiviral action of 5'-noraristeromycin and provide guidance for future geminal-difluoro analog design. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.011
• 作为产物：
  描述：

  (1S,2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(6-chloropurin-9-yl)cyclopentane-1,2-diol 在 ammonium cerium(IV) nitrate 、 二乙胺基三氟化硫 、 二正丁基氧化锡 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 水 、 乙腈 、 苯 为溶剂， 反应 74.0h， 生成 (1S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(6-chloropurin-9-yl)-2,2-difluorocyclopentanol
  参考文献：
  名称：

  3′-Fluoro-3′-deoxy-5′-noraristeromycin derivatives: Synthesis and antiviral analysis

  摘要：

  The promising antiviral properties of 3'-fluoro-3'-deoxyadenosine and 4',4'-difluoro-4'-deoxy-5'-noraristeromycin prompted the synthesis of the corresponding 3'-fluoro derivatives of 5'-noraristeromycin. These target compounds, which were prepared from the same readily accessible cyclopentenol, were found to be inactive when subjected to 31 viral assays. The results have some implications on the mechanism of antiviral action of 5'-noraristeromycin and provide guidance for future geminal-difluoro analog design. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.011