2-(2-Nitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester | 199122-98-0

• 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: 2-(2-Nitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester
• 英文别名: [(2R,3S,5R)-3-hydroxy-5-[6-[2-(4-nitrophenyl)ethoxycarbonylamino]purin-9-yl]oxolan-2-yl]methyl 2-(2-nitrophenyl)ethanesulfonate
• CAS: 199122-98-0
• 化学式: C₂₇H₂₇N₇O₁₁S
• 分子量: 657.618
• InChiKey: AMFVTTLHFABUMD-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  255
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2-(2-硝基苯基)乙醇 在 氯化亚砜 、 氯 、 sodium thiosulfate 作用下， 生成 2-(2-Nitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  New Photolabile Protecting Groups in Nucleoside and Nucleotide Chemistry—Synthesis, Cleavage Mechanisms and Applications

  摘要：

  New photolabile protecting groups have been found in the 2-(2-nitrophenyl)ethoxycarbonyl and the 2-(2-nitrophenyl)ethylsulfonyl group, respectively. The influence of substituents at the phenyl ring as well as the side-chain has been investigated regarding the photolysis rates on irradiation at 365 mn. beta-Branching in the side-chain leads to highly increased rates of photodeprotection. A new type of photocleavage mechanism consisting of a photoinduced beta-elimination process is proposed.

  DOI：

  10.1080/07328319808004738

文献信息

• New Photolabile Protecting Groups in Nucleoside and Nucleotide Chemistry—Synthesis, Cleavage Mechanisms and Applications
  作者：H. Giegrich、S. Eisele-Bühler、Chr Hermann、E. Kvasyuk、R. Charubala、W. Pfleiderer

  DOI：10.1080/07328319808004738

  日期：1998.9

  New photolabile protecting groups have been found in the 2-(2-nitrophenyl)ethoxycarbonyl and the 2-(2-nitrophenyl)ethylsulfonyl group, respectively. The influence of substituents at the phenyl ring as well as the side-chain has been investigated regarding the photolysis rates on irradiation at 365 mn. beta-Branching in the side-chain leads to highly increased rates of photodeprotection. A new type of photocleavage mechanism consisting of a photoinduced beta-elimination process is proposed.