2-amino-6-chloro-9-<5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-β-D-arabinofuranosyl>-9H-purine | 156900-24-2

• 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-amino-6-chloro-9-<5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-β-D-arabinofuranosyl>-9H-purine
• CAS: 156900-24-2
• 化学式: C₁₆H₂₅ClFN₅O₃Si
• 分子量: 417.943
• InChiKey: XXHHYUPMBQYWHB-SZRLZVLASA-N

物化性质

• 沸点：
  572.4±60.0 °C(predicted)
• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  108.31
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-amino-6-chloro-9-<5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-β-D-arabinofuranosyl>-9H-purine 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 tributylsilane 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 27.0h， 生成 2-amino-6-chloro-9-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl>-9H-purine
  参考文献：
  名称：

  Chemistry and Anti-HIV Activity of 2′-β-Fluoro-2′,3′-dideoxyguanosine

  摘要：

  The 2'-beta-fluoro analogue of 2',3'-dideoxyguanosine has been prepared by two synthetic routes. This compound and two analogues have anti-HIV activity in at least two of three host cell systems used (ATH8, CEM, PEL). These compounds, as well as their ddGuo parents, have been characterized with regard to their acid-stabilities, octanol-water partition coefficients, and enzyme substrate properties for adenosine deaminase and purine nucleoside phosphorylase. F-ddGuo analogues are less potent but more stable than their non-fluorinated parent compounds.

  DOI：

  10.1080/15257779408013236
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 6-氯-9-(2-脱氧-2-氟-beta-D-阿拉伯呋喃糖基)-9H-嘌呤-2-胺 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以13%的产率得到9-[(2R,3S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-fluoro-tetrahydro-furan-2-yl]-6-chloro-9H-purin-2-ylamine
  参考文献：
  名称：

  Chemistry and Anti-HIV Activity of 2′-β-Fluoro-2′,3′-dideoxyguanosine

  摘要：

  The 2'-beta-fluoro analogue of 2',3'-dideoxyguanosine has been prepared by two synthetic routes. This compound and two analogues have anti-HIV activity in at least two of three host cell systems used (ATH8, CEM, PEL). These compounds, as well as their ddGuo parents, have been characterized with regard to their acid-stabilities, octanol-water partition coefficients, and enzyme substrate properties for adenosine deaminase and purine nucleoside phosphorylase. F-ddGuo analogues are less potent but more stable than their non-fluorinated parent compounds.

  DOI：

  10.1080/15257779408013236