[(2R,3S,5R)-3-hydroxy-5-[4-[2-(4-nitrophenyl)ethoxycarbonylamino]-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl 2-(4-chloro-2-nitrophenyl)ethanesulfonate | 199123-01-8

• 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: [(2R,3S,5R)-3-hydroxy-5-[4-[2-(4-nitrophenyl)ethoxycarbonylamino]-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl 2-(4-chloro-2-nitrophenyl)ethanesulfonate
• CAS: 199123-01-8
• 化学式: C₂₆H₂₆ClN₅O₁₂S
• 分子量: 668.038
• InChiKey: DWPCHEDMSGHHBI-WMTXJRDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  45.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  232.33
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  4-chloro-1-(2-chloroethyl)-2-nitro-benzene 在 氯 、 sodium thiosulfate 作用下， 生成 [(2R,3S,5R)-3-hydroxy-5-[4-[2-(4-nitrophenyl)ethoxycarbonylamino]-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl 2-(4-chloro-2-nitrophenyl)ethanesulfonate
  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