(3R,4R,5R)-4-cyano-4-((methylsulfonyl)oxy)-5-((tosyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate | 1375389-68-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4R,5R)-4-cyano-4-((methylsulfonyl)oxy)-5-((tosyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate
• CAS: 1375389-68-6
• 化学式: C₁₈H₂₁NO₁₁S₂
• 分子量: 491.497
• InChiKey: LGWAZAOWABFEBV-UJJTZGENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.16
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  172.36
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-4-cyano-4-((methylsulfonyl)oxy)-5-((tosyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.17h， 生成 ((5R,6R,8R,9R)-4-amino-9-((tert-butyldimethylsilyl)oxy)-8-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-6-yl)methyl 4-methylbenzenesulfonate
  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 Finally, the thymine of the prototype compound has been replaced by N-3-methylthymine, uracil or thiophenyl.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
• 作为产物：
  描述：

  5-O-tosyl-3-C-cyano-3-O-mesyl-D-ribofuranose 、 乙酸酐 在 吡啶 作用下， 生成 (3R,4R,5R)-4-cyano-4-((methylsulfonyl)oxy)-5-((tosyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate
  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