[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[(E)-2-ethoxycarboxyvinyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide) | 672307-73-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[(E)-2-ethoxycarboxyvinyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)
• CAS: 672307-73-2
• 化学式: C₂₉H₄₉N₃O₁₀SSi₂
• 分子量: 687.959
• InChiKey: DXWVBAXMRLOPDD-XNXFRXCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  167.38
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[(E)-2-ethoxycarboxyvinyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide) 以 甲醇 为溶剂， 反应 0.5h， 以60%的产率得到[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[(Z)-2-ethoxycarboxyvinyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)
  参考文献：
  名称：

  Novel N-3 Substituted TSAO-T Derivatives: Synthesis and Anti-HIV-Evaluation

  摘要：

  Novel derivatives of the anti-HIV-1 agent, TSAO-T, bearing at the N-3 position alkylating groups or photoaffinity labels were prepared and evaluated for their anti-HIV activity. All of these compounds demonstrated pronounced anti-HIV-1 activity and inhibited HIV-1 RT; however, we were unable to detect stable covalent linkages between inhibitor and enzyme. In addition, compounds with an alcohol functional group connected to the N-3 position through a cis or trans double bond have been prepared. These compounds have been useful to study how the conformational restriction of the linker affects in the interaction between the N-3 substituent and the HIV-1 RT enzyme.

  DOI：

  10.1080/15257770801943990
• 作为产物：
  描述：

  1-[(5R,6R,7R,9R)-4-氨基-6-(叔丁基-二甲基硅烷基)氧基-9-[(叔丁基-二甲基硅烷基)氧基甲基]-2,2-二氧代-1,8-二氧杂-2-硫杂螺[4.4]壬-3-烯-7-基]-5-甲基嘧啶-2,4-二酮 、 丙炔酸乙酯 在 4-二甲氨基吡啶 作用下， 反应 1.5h， 以82%的产率得到[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[(E)-2-ethoxycarboxyvinyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)
  参考文献：
  名称：

  Novel N-3 Substituted TSAO-T Derivatives: Synthesis and Anti-HIV-Evaluation

  摘要：

  Novel derivatives of the anti-HIV-1 agent, TSAO-T, bearing at the N-3 position alkylating groups or photoaffinity labels were prepared and evaluated for their anti-HIV activity. All of these compounds demonstrated pronounced anti-HIV-1 activity and inhibited HIV-1 RT; however, we were unable to detect stable covalent linkages between inhibitor and enzyme. In addition, compounds with an alcohol functional group connected to the N-3 position through a cis or trans double bond have been prepared. These compounds have been useful to study how the conformational restriction of the linker affects in the interaction between the N-3 substituent and the HIV-1 RT enzyme.

  DOI：

  10.1080/15257770801943990