5'-O-(1,1-dianisyl-2,2,2-trichloroethyl)-3'-O-(N,N-dimethylaminotrifluoromethylphosphine) thymidine | 164798-90-7

• 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: 5'-O-(1,1-dianisyl-2,2,2-trichloroethyl)-3'-O-(N,N-dimethylaminotrifluoromethylphosphine) thymidine
• 英文别名: 1-[(2R,4S,5R)-4-[dimethylamino(trifluoromethyl)phosphanyl]oxy-5-[[2,2,2-trichloro-1,1-bis(4-methoxyphenyl)ethoxy]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 164798-90-7；164798-91-8
• 化学式: C₂₉H₃₂Cl₃F₃N₃O₇P
• 分子量: 728.917
• InChiKey: RDJATSLQVXMGSV-XIEUVFHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  104.25
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5'-O-(1,1-dianisyl-2,2,2-trichloroethyl)-3'-O-(N,N-dimethylaminotrifluoromethylphosphine) thymidine 在 苯甲酰氯 作用下， 以 氘代氯仿 为溶剂， 反应 5.0h， 生成 1-[(2R,4S,5R)-4-[chloro(trifluoromethyl)phosphanyl]oxy-5-[[2,2,2-trichloro-1,1-bis(4-methoxyphenyl)ethoxy]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  The 1,1-Dianisyl-2,2,2-trichloroethyl Moiety as a New Protective Group for the Synthesis of Dinucleostde Trifluoromethylphosphonates

  摘要：

  The new 1,1-Dianisyl-2,2,2-trichloroethyl moiety (DATE) is used as an acid and base stable protective group for nucleosides. 5'-O-DATE-thymidine and 3'-O-acetylthymidine are phosphorylated with CF3P(NR(2))(2) to the corresponding thymidine trifluoromethylphosphonous amidites. These building blocks are coupled with appropriate protected thymidines to a dinucleotide trifluoromethylphosphonate.

  DOI：

  10.1080/07328319608002391
• 作为产物：
  描述：

  beta-胸苷 在 吡啶 、 四氮唑 、 silver(I) 4-methylbenzenesulfonate 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 5'-O-(1,1-dianisyl-2,2,2-trichloroethyl)-3'-O-(N,N-dimethylaminotrifluoromethylphosphine) thymidine
  参考文献：
  名称：

  The 1,1-Dianisyl-2,2,2-trichloroethyl Moiety as a New Protective Group for the Synthesis of Dinucleostde Trifluoromethylphosphonates

  摘要：

  The new 1,1-Dianisyl-2,2,2-trichloroethyl moiety (DATE) is used as an acid and base stable protective group for nucleosides. 5'-O-DATE-thymidine and 3'-O-acetylthymidine are phosphorylated with CF3P(NR(2))(2) to the corresponding thymidine trifluoromethylphosphonous amidites. These building blocks are coupled with appropriate protected thymidines to a dinucleotide trifluoromethylphosphonate.

  DOI：

  10.1080/07328319608002391

文献信息

• Studies on trifluoromethylphosphonamidite analogues as building blocks in oligonucleotide synthesis
  作者：Michael Mayer、Ivar Ugi、Wolfgang Richter

  DOI：10.1016/0040-4039(95)00186-g

  日期：1995.3

  The phosphorylating reagents CF3P(NMe(2))Cl and CF3P(NEt(2))Cl are used to phosphorylate the 3'-hydroxyl moiety of several protected 2'-deoxynucleosides yielding the corresponding nucleoside trifluoromethyl phosphonamidites. Their scope and limitations towards amidite activation are investigated but, however, their behavior is completely different to commonly used nucleoside phosphorus amidites.