methyl (2S)-2-[[2-cyanoethoxy-[[(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]amino]-3-(1H-indol-3-yl)propanoate | 196878-06-5

• 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-[[2-cyanoethoxy-[[(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 196878-06-5
• 化学式: C₂₅H₂₉FN₅O₈P
• 分子量: 577.506
• InChiKey: RRUWGDRHMORKGU-SKFIWXLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  172
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[2-cyanoethoxy-[[(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]amino]-3-(1H-indol-3-yl)propanoate 在 氨 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以97%的产率得到3'-fluoro-3'-deoxythymidine-5'-(ammonium methoxytryptophanyl) phosphoramidate
  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：

  3’-脱氧-3-氟胸苷 在 四氮唑 、 甲醇 、 碘 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl (2S)-2-[[2-cyanoethoxy-[[(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]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

文献信息

• A Phosphoramidite-Based Synthesis of Phosphoramidate Amino Acid Diesters of Antiviral Nucleosides
  作者：Timothy W. Abraham、Carston R. Wagner

  DOI：10.1080/15257779408010671

  日期：1994.9

  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.