3'-azido-3',5'-dideoxythymidine 5'-triphosphate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3'-azido-3',5'-dideoxythymidine 5'-triphosphate
• 英文别名: [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl-[hydroxy(phosphonooxy)phosphoryl]oxy-phosphinic acid；[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl-[hydroxy(phosphonooxy)phosphoryl]oxyphosphinic acid
• 化学式: C₁₀H₁₆N₅O₁₂P₃
• 分子量: 491.185
• InChiKey: YHJUMQWPHWITST-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  224
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  [(2S,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-imidazol-1-yl-phosphinic acid 在 六甲基磷酰三胺 、 三丁基焦磷酸铵 作用下， 反应 4.0h， 生成 3'-azido-3',5'-dideoxythymidine 5'-triphosphate
  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