2',3'-dideoxy-3'-fluoro-β-L-adenosine | 216571-37-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',3'-dideoxy-3'-fluoro-β-L-adenosine
• 英文别名: L-3'-fluoro-ddA；L-2',3'-dideoxy-3'-fluoroadenosine；[(2S,3R,5S)-5-(6-aminopurin-9-yl)-3-fluoro-tetrahydrofuran-2-yl]methanol；[(2S,3R,5S)-5-(6-aminopurin-9-yl)-3-fluorooxolan-2-yl]methanol
• CAS: 216571-37-8
• 化学式: C₁₀H₁₂FN₅O₂
• 分子量: 253.236
• InChiKey: CTDUJDNZPPZTAV-VQVTYTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl methoxyalaninyl phosphorochloridate 、 2',3'-dideoxy-3'-fluoro-β-L-adenosine 在 吡啶 、 叔丁基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以68%的产率得到9-(2',3'-dideoxy-3'-fluoro-β-L-ribofuranosyl)adenine-5'-[phenyl-(methoxy-L-alaninyl)]phosphoramidate
  参考文献：
  名称：

  Phosphoramidate Protides of 2′,3′-Dideoxy-3′-fluoroadenosine and Related Nucleosides with Potent Activity Against HIV and HBV

  摘要：

  Syntheses of phosphoramidate protides of several 2',3'-dideoxy-3'-fluoroadenosine derivatives by treatment of the nucleoside with phosphorochloridates in the presence of pyridine and t-BuMgCl is described. Several of these protides showed significantly improved antiviral potency over the parent nucleoside against HIV and HBV. Especially marked was the improvement in potency of phosphoramidate protides of 2',3'-dideoxy-3'-fluoroadenosine against both HIV and HBV.

  DOI：

  10.1081/ncn-120025242
• 作为产物：
  描述：

  9-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)adenine 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 (Me₃Si(3SiH 、 氨 、 一水合肼 、 溶剂黄146 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 硫代氯甲酸苯酯 作用下， 以 吡啶 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 生成 2',3'-dideoxy-3'-fluoro-β-L-adenosine
  参考文献：
  名称：

  Unnatural β-L-Enantiomers of Nucleoside Analogues as Potent Anti-Hepatitis B Virus Agents

  摘要：

  Several 2'- or 3'-substituted 2',3'-dideoxy-beta-L-nucleosides bearing adenine as the base were stereospecifically synthesized and their antiviral properties examined. Two of them, namely 2'-azido- and 3'-azido-2',3'-dideoxy-beta-L-adenosine (2'-N-3-beta-L-ddA and 3'-N-3-beta-L-ddA) were found to have some anti-hepatitis B virus (HBV) activity in cell culture.

  DOI：

  10.1080/07328319808004708

文献信息

• Synthesis of 2′,3′-dideoxy-3′-fluoro-l-ribonucleosides as potential antiviral agents from d-sorbitol
  作者：Byoung K Chun、Raymond F Schinazi、Yung-Chi Cheng、Chung K Chu

  DOI：10.1016/s0008-6215(99)00312-2

  日期：2000.8

  2',3'-Dideoxy-3'-fluoro-L-ribonucleosides were synthesized as potential antiviral agents. The key intermediate, methyl 5-O-benzoyl-2,3-dideoxy-3-fluoro-L-ribofuranoside, which was prepared from D-sorbitol, was condensed with pyrimidine and purine bases to obtain the respective nucleosides. Among them, the cytosine analogue 2',3'-dideoxy-3'-fluoro-alpha-L-cytidine showed a moderate anti-HBV activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Unnatural β-L-Enantiomers of Nucleoside Analogues as Potent Anti-Hepatitis B Virus Agents
  作者：G. Gosselin、V. Boudou、J-F Griffon、G. Pavia、C. Pierra、J-L Imbach、A. Faraj、J-P Sommadossi

  DOI：10.1080/07328319808004708

  日期：1998.9

  Several 2'- or 3'-substituted 2',3'-dideoxy-beta-L-nucleosides bearing adenine as the base were stereospecifically synthesized and their antiviral properties examined. Two of them, namely 2'-azido- and 3'-azido-2',3'-dideoxy-beta-L-adenosine (2'-N-3-beta-L-ddA and 3'-N-3-beta-L-ddA) were found to have some anti-hepatitis B virus (HBV) activity in cell culture.
• Phosphoramidate Protides of 2′,3′-Dideoxy-3′-fluoroadenosine and Related Nucleosides with Potent Activity Against HIV and HBV
  作者：Kristjan S. Gudmundsson、Susan M. Daluge、Lance C. Johnson、Robert Jansen、Richard Hazen、Lynn D. Condreay、Christopher McGuigan

  DOI：10.1081/ncn-120025242

  日期：2003.10.1

  Syntheses of phosphoramidate protides of several 2',3'-dideoxy-3'-fluoroadenosine derivatives by treatment of the nucleoside with phosphorochloridates in the presence of pyridine and t-BuMgCl is described. Several of these protides showed significantly improved antiviral potency over the parent nucleoside against HIV and HBV. Especially marked was the improvement in potency of phosphoramidate protides of 2',3'-dideoxy-3'-fluoroadenosine against both HIV and HBV.