5'-O-(1,1-dianisyl-2,2,2-trichloroethyl)-3'-O-(N,N-diethylaminotrifluoromethylphosphine) thymidine | 175601-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5'-O-(1,1-dianisyl-2,2,2-trichloroethyl)-3'-O-(N,N-diethylaminotrifluoromethylphosphine) thymidine
• 英文别名: 1-[(2R,4S,5R)-4-[diethylamino(trifluoromethyl)phosphanyl]oxy-5-[[2,2,2-trichloro-1,1-bis(4-methoxyphenyl)ethoxy]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 175601-08-8；175601-09-9
• 化学式: C₃₁H₃₆Cl₃F₃N₃O₇P
• 分子量: 756.971
• InChiKey: LVAZOYQROODYIZ-BOFCZRPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  48.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 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-diethylaminotrifluoromethylphosphine) thymidine 在 3-(2,4-dichlorophenyl)-2-toluenesulfonyl oxaziridine 、 苯甲酰氯 、 三乙胺 作用下， 以 氘代氯仿 为溶剂， 生成 [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[2,2,2-trichloro-1,1-bis(4-methoxyphenyl)ethoxy]methyl]oxolan-3-yl]oxy-(trifluoromethyl)phosphoryl]oxymethyl]oxolan-3-yl] acetate
  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：

  1,1-dianisyl-2,2,2-trichloroethyl chloride 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-diethylaminotrifluoromethylphosphine) 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