1-[6,6-difluoro-6-(β,γ-difluoromethylenetriphosphono)-2,3,5,6-tetradeoxy-β-D-allofuranosyl]thymine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 1-[6,6-difluoro-6-(β,γ-difluoromethylenetriphosphono)-2,3,5,6-tetradeoxy-β-D-allofuranosyl]thymine
• 英文别名: [[[[1,1-difluoro-2-[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]ethyl]-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]-difluoro-methyl]phosphonic acid；[[[[1,1-difluoro-2-[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethyl]-hydroxyphosphoryl]oxy-hydroxyphosphoryl]-difluoromethyl]phosphonic acid
• 化学式: C₁₂H₁₇F₄N₂O₁₁P₃
• 分子量: 534.189
• InChiKey: ULRAIIGHNAMJFJ-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  200
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  {1,1-Difluoro-2-[(S)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-phosphonic acid; compound with triethyl-amine 、 bis(tributylammonium) difluoromethylenediphosphonate 在 六甲基磷酰三胺 、 N,N'-羰基二咪唑 作用下， 反应 12.0h， 生成 1-[6,6-difluoro-6-(β,γ-difluoromethylenetriphosphono)-2,3,5,6-tetradeoxy-α-D-allofuranosyl]thymine 、 1-[6,6-difluoro-6-(β,γ-difluoromethylenetriphosphono)-2,3,5,6-tetradeoxy-β-D-allofuranosyl]thymine
  参考文献：
  名称：

  Synthesis of 5'-Triphosphate Mimics (P3Ms) of 3'-Azido-3',5'-Dideoxythymidine and 3',5'-Dideoxy-5'-Difluoromethylenethymidine as HIV-1 Reverse Transcriptase Inhibitors

  摘要：

  3'-Azido-3,5-dideoxythymidine 5-phosphonate and 3',5-dideoxy-5-difluoromethylenethymidine 5'-phosphonate were prepared by multistep syntheses. The nucleoside 5-phosphonates were converted to their triphosphates and triphosphate mimics (P3Ms) containing beta,gamma-difluoromethylene, beta,gamma-dichloromethylene, or beta,gamma-imodo by condensation with pyrophosphate or Pyrophosphate mimics, respectively. Inhibition of HIV-1 reverse transcriptase by the nucleoside P3Ms is briefly discussed.

  DOI：

  10.1081/ncn-200055707

文献信息

• Synthesis of 5'-Triphosphate Mimics (P3Ms) of 3'-Azido-3',5'-Dideoxythymidine and 3',5'-Dideoxy-5'-Difluoromethylenethymidine as HIV-1 Reverse Transcriptase Inhibitors
  作者：Vivek Rajwanshi、Marija Prhavc、Patrick Fagan、Jennifer Brooks、Tiffany Hurd、P. Dan Cook、Guangyi Wang

  DOI：10.1081/ncn-200055707

  日期：2005.3.1

  3'-Azido-3,5-dideoxythymidine 5-phosphonate and 3',5-dideoxy-5-difluoromethylenethymidine 5'-phosphonate were prepared by multistep syntheses. The nucleoside 5-phosphonates were converted to their triphosphates and triphosphate mimics (P3Ms) containing beta,gamma-difluoromethylene, beta,gamma-dichloromethylene, or beta,gamma-imodo by condensation with pyrophosphate or Pyrophosphate mimics, respectively. Inhibition of HIV-1 reverse transcriptase by the nucleoside P3Ms is briefly discussed.