3'-deoxy-2',3'-didehydrothymidine 5'-fluorophosphoridate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3'-deoxy-2',3'-didehydrothymidine 5'-fluorophosphoridate
• 英文别名: fluoro-[[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]phosphinic acid；fluoro-[[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]phosphinic acid
• 化学式: C₁₀H₁₂FN₂O₆P
• 分子量: 306.187
• InChiKey: ZIZQTVORFUXCRZ-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  司他夫定 在 2,4,6-三异丙基苯磺酰氯 、 fluorophosphoric acid tri-n-butylammonium salt 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 以44%的产率得到3'-deoxy-2',3'-didehydrothymidine 5'-fluorophosphoridate
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Some Fluorinated Nucleotide Derivatives

  摘要：

  A number of 3'-fluoro-3'-deoxythymidine 5'-phosphonates and nucleoside 5'-phosphorofluoridates were prepared to study their ability to inhibit replication of HIV-1. Compounds, the 5'-phosphorofluoridates of 3'-azido-3'-deoxythymidine (VIIIc), 3'-fluoro-3'-deoxythymidine (VIIId) and 3'-deoxy-2',3'-didehydrothymidine (VIIIe), exhibit potent anti-HTV-1 activities.

  DOI：

  10.1080/15257779408013244

文献信息

• Synthesis and Antiviral Activity of Some Fluorinated Nucleotide Derivatives
  作者：Natalia Dyatkina、Andrey Arzumanov、Alexander Krayevsky、Bryan O'Hara、Yacov Gluzman、Penny Baron、Clarinda MacLow、Bruce Polsky

  DOI：10.1080/15257779408013244

  日期：1994.3

  A number of 3'-fluoro-3'-deoxythymidine 5'-phosphonates and nucleoside 5'-phosphorofluoridates were prepared to study their ability to inhibit replication of HIV-1. Compounds, the 5'-phosphorofluoridates of 3'-azido-3'-deoxythymidine (VIIIc), 3'-fluoro-3'-deoxythymidine (VIIId) and 3'-deoxy-2',3'-didehydrothymidine (VIIIe), exhibit potent anti-HTV-1 activities.