N-(9-((2S,3S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxy-4-methylenetetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide | 1256086-98-2

• 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: N-(9-((2S,3S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxy-4-methylenetetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide
• CAS: 1256086-98-2
• 化学式: C₃₄H₃₅N₅O₄Si
• 分子量: 605.769
• InChiKey: ZLKIFAUPOHVVJY-ZFQPXVTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  111.39
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(9-((2S,3S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxy-4-methylenetetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 、 甲基磺酰氯 在 三乙胺 作用下， 以 乙腈 为溶剂， 以78%的产率得到(2S,3S,5S)-2-(6-benzamido-9H-purin-9-yl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-methylenetetrahydrofuran-3-yl methanesulfonate
  参考文献：
  名称：

  Synthesis and antiviral evaluation of α-d-2′,3′-didehydro-2′,3′-dideoxy-3′-C-hydroxymethyl nucleosides

  摘要：

  We have identified a selective S(N)2' reaction triggered by iodide ion that leads to the ring-opening of 2,2'-anhydro-alpha-nucleosides. By applying the method, we have synthesized alpha-D-2',3'-didehydro-2',3'-dideoxy- 3'-C-hydroxymethyl nucleosides, designed as potential antiviral agents. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.071
• 作为产物：
  描述：

  在 甲醇 、 potassium carbonate 作用下， 生成 N-(9-((2S,3S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxy-4-methylenetetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide
  参考文献：
  名称：

  Synthesis and antiviral evaluation of α-d-2′,3′-didehydro-2′,3′-dideoxy-3′-C-hydroxymethyl nucleosides

  摘要：

  We have identified a selective S(N)2' reaction triggered by iodide ion that leads to the ring-opening of 2,2'-anhydro-alpha-nucleosides. By applying the method, we have synthesized alpha-D-2',3'-didehydro-2',3'-dideoxy- 3'-C-hydroxymethyl nucleosides, designed as potential antiviral agents. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.071