3'-O-acetyl-5'-O-(N,N-diethylaminotrifluoromethylphosphine) thymidine | 175601-10-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 3'-O-acetyl-5'-O-(N,N-diethylaminotrifluoromethylphosphine) thymidine
• 英文别名: [(2R,3S,5R)-2-[[diethylamino(trifluoromethyl)phosphanyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 175601-10-2；175601-11-3
• 化学式: C₁₇H₂₅F₃N₃O₆P
• 分子量: 455.371
• InChiKey: UYHRHZCDOOAPAZ-CMXKDALQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  102.86
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-5'-O-(N,N-diethylaminotrifluoromethylphosphine) thymidine 在 3-(2,4-dichlorophenyl)-2-toluenesulfonyl oxaziridine 、 苯甲酰氯 作用下， 以 氘代氯仿 为溶剂， 生成 [(2R,3S,5R)-2-[[chloro(trifluoromethyl)phosphoryl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)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：

  bis(diethylamino)trifluoromethylphosphine 、 3'-O-acetylthymidine 在 四氮唑 作用下， 以77%的产率得到3'-O-acetyl-5'-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