替诺福韦杂质W | 1244022-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 替诺福韦杂质W
• 英文名称: ((Hydroxy((((R)-1-(6-((hydroxymethyl)amino)-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphoryl)oxy)methyl isopropyl carbonate
• 英文别名: [(2R)-1-[6-(hydroxymethylamino)purin-9-yl]propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphinic acid
• CAS: 1244022-55-6
• 化学式: C₁₅H₂₄N₅O₈P
• 分子量: 433.358
• InChiKey: UKJXDNGUPTYVFW-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  167
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  腺嘌呤 在 三甲基氯硅烷 、 magnesium 2-methylpropan-2-olate 、 三乙胺 、 sodium bromide 、 sodium hydroxide 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 替诺福韦杂质W 、 6N-羟甲基替诺福韦二吡呋酯
  参考文献：
  名称：

  Process Improvements for the Manufacture of Tenofovir Disoproxil Fumarate at Commercial Scale

  摘要：

  The three-step manufacturing process used in the synthesis of tenofovir disoproxil fumarate (1) was studied and optimized, leading to a more productive and robust process. The yield was improved from about 13% overall to 24%. Key process improvements identified included implementation of a telescoped process for the second stage that obviated the need for an extraction and solvent exchange, and significant optimization of the final reaction, including the beneficial effect of adding a quaternary ammonium salt to the alkylation reaction and development of a nonaqueous process for removal of NMP and triethylamine from the product mixture to decrease the level of decomposition of product during the isolation.

  DOI：

  10.1021/op1001337