3',5'-bis-O-(2-(2,4-dichloro-6-nitrophenyl)ethoxycarbonyl)thymidine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3',5'-bis-O-(2-(2,4-dichloro-6-nitrophenyl)ethoxycarbonyl)thymidine
• 英文别名: [(2R,3S,5R)-3-[2-(2,4-dichloro-6-nitrophenyl)ethoxycarbonyloxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2-(2,4-dichloro-6-nitrophenyl)ethyl carbonate
• 化学式: C₂₈H₂₄Cl₄N₄O₁₃
• 分子量: 766.33
• InChiKey: BAYWEOXLQXMFTF-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  221
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2-(2,4-dichloro-6-nitrophenyl)ethanol 生成 3',5'-bis-O-(2-(2,4-dichloro-6-nitrophenyl)ethoxycarbonyl)thymidine
  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

• NUCLEOSID-DERIVATE MIT PHOTOLABILEN SCHUTZGRUPPEN
  申请人：Pfleiderer, Wolfgang

  公开号：EP0797580B1

  公开（公告）日：2002-04-10
• US5763599A
  申请人：——

  公开号：US5763599A

  公开（公告）日：1998-06-09
• 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.