1-((3aS,5aR,7R,8R,8aR)-8-(((2,3-dimethylbutan-2-yl)dimethylsilyl)oxy)-3a-ethoxy-2,2-dioxidohexahydro-3H-furo[3,2-c][1,2]oxathiolo[4,5-b]pyrrol-7-yl)-5-methylpyrimidine-2,4(1H,3H)-dione | 1375389-67-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((3aS,5aR,7R,8R,8aR)-8-(((2,3-dimethylbutan-2-yl)dimethylsilyl)oxy)-3a-ethoxy-2,2-dioxidohexahydro-3H-furo[3,2-c][1,2]oxathiolo[4,5-b]pyrrol-7-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS: 1375389-67-5
• 化学式: C₂₂H₃₇N₃O₈SSi
• 分子量: 531.703
• InChiKey: PFRVMZWOSACBCN-VQMFYWGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  137.95
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  5',N⁴''-cyclo{1-[2'-O-(tert-butyldimethylsilyl)-5'-deoxy-β-D-ribofuranosyl]thymine}-3'-spiro-5''-(4''-amino-4''S-ethoxy-1'',2''-oxathiolane-2'',2''-dioxide) 在 甲醇 、 4-二甲氨基吡啶 、 氟化铵 作用下， 以 乙腈 为溶剂， 生成 1-((3aS,5aR,7R,8R,8aR)-8-(((2,3-dimethylbutan-2-yl)dimethylsilyl)oxy)-3a-ethoxy-2,2-dioxidohexahydro-3H-furo[3,2-c][1,2]oxathiolo[4,5-b]pyrrol-7-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Selective inhibition of Human Immunodeficiency Virus type 1 (HIV-1) by a novel family of tricyclic nucleosides

  摘要：

  Nucleoside 1, with an unusual tricyclic carbohydrate moiety, specifically inhibits HIV-1 replication while being inactive against HIV-2 or other (retro) viruses. In an attempt to increase the inhibitory efficacy against HIV-1, and to further explore the structural features required for anti-HIV-1 activity, different types of modifications have been carried out on this prototype compound. These include substitution of the ethoxy group at the C-4" position by alkoxy groups of different length, branching, conformational freedom or functionalization. In addition, the 4"-ethoxy group has been removed or substituted by other functional groups. The role of the tert-butyldimethylsilyl (TBDMS) group at the 2' position has also been studied by preparing the corresponding 2'-deprotected derivative or by replacing it by other silyl (tert-hexyldimethylsilyl) or acyl (acetyl) moieties. Finally, the thymine of the prototype compound has been replaced by N-3-methylthymine, uracil or thiophenyl. Some of these compounds were endowed with a 6- to 7-fold higher selectivity than the prototype 1. The tricyclic nucleosides here described represent a novel type of selective anti HIV-1 inhibitors, targeted at the HIV-1-encoded reverse transcriptase. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.antiviral.2011.05.002