methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy-(2-cyanoethoxy)phosphoryl]amino]-3-(1H-indol-3-yl)propanoate | 196878-01-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy-(2-cyanoethoxy)phosphoryl]amino]-3-(1H-indol-3-yl)propanoate
• 英文别名: methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-(2-cyanoethoxy)phosphoryl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 196878-01-0
• 化学式: C₂₅H₂₉N₈O₈P
• 分子量: 600.528
• InChiKey: LAUPZWJCAHDSFU-YNFPKLKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  186
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy-(2-cyanoethoxy)phosphoryl]amino]-3-(1H-indol-3-yl)propanoate 在 氨 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以86%的产率得到2(S)-(hydroxy(3-deoxy-3-azidothymidyl)phosphorylamino)-3-(3-indolyl)propionic acid methyl ester
  参考文献：
  名称：

  A Phosphoramidite-Based Synthesis of Phosphoramidate Amino Acid Diesters of Antiviral Nucleosides

  摘要：

  A general synthetic procedure is presented for the preparation of 5'-amino acid phosphoramidates of zidovudine (AZT), 3'-deoxy-2',3'-didehydrothymidine (D4T), and 3'-fluoro-3'-deoxythymidine (FLT) from their corresponding phosphoramidites. These water soluble amino acid phosphoramidates are more non-polar than the parent nucleoside and exhibit high stability in aqueous media.

  DOI：

  10.1080/15257779408010671
• 作为产物：
  描述：

  齐多夫定 在 四氮唑 、 甲醇 、 碘 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy-(2-cyanoethoxy)phosphoryl]amino]-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  A Phosphoramidite-Based Synthesis of Phosphoramidate Amino Acid Diesters of Antiviral Nucleosides

  摘要：

  A general synthetic procedure is presented for the preparation of 5'-amino acid phosphoramidates of zidovudine (AZT), 3'-deoxy-2',3'-didehydrothymidine (D4T), and 3'-fluoro-3'-deoxythymidine (FLT) from their corresponding phosphoramidites. These water soluble amino acid phosphoramidates are more non-polar than the parent nucleoside and exhibit high stability in aqueous media.

  DOI：

  10.1080/15257779408010671