(1S,5S,6S,7R,8R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-8-(4-fluorophenoxy)carbothioyloxy-2-oxabicyclo[3.2.1]octan-3-one | 158469-40-0

• 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: (1S,5S,6S,7R,8R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-8-(4-fluorophenoxy)carbothioyloxy-2-oxabicyclo[3.2.1]octan-3-one
• CAS: 158469-40-0
• 化学式: C₂₃H₃₃FO₇SSi
• 分子量: 500.661
• InChiKey: SOWJJUZEUJERIN-FLNBYBTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S,5S,6S,7R,8R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-8-(4-fluorophenoxy)carbothioyloxy-2-oxabicyclo[3.2.1]octan-3-one 在 偶氮二异丁腈 、 三正丁基氢锡 、 lithium perchlorate 、 双(三甲基硅烷基)氨基钾 、 spiro[(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3'-N-phenylsulfonyloxaziridine] 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 生成 (1S,4S,5R,6S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-4-hydroxy-4-prop-2-enyl-2-oxabicyclo[3.2.1]octan-3-one
  参考文献：
  名称：

  Free Radical Methodology for Carbohydrate to Carbocycle Transformations: An Efficient Synthesis of the Tricyclic Dihydrofuran Portion of Azadirachtin

  摘要：

  Iodo lactone 6b, derived from D-galactal, undergoes tin hydride mediated transannular radical cyclization to give the tricyclic lactone 7, which is easily converted into an advanced precursor of the tricyclic dihydrofuran portion of the potent insect antifeedant azadirachtin (1).

  DOI：

  10.1021/jo00097a007
• 作为产物：
  描述：

  (1R,2S,6S,7R,8S,9R)-7-[tert-butyl(dimethyl)silyl]oxy-9-methoxy-5,10-dioxatricyclo[4.4.0.02,8]decan-4-one 在 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (1S,5S,6S,7R,8R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-8-(4-fluorophenoxy)carbothioyloxy-2-oxabicyclo[3.2.1]octan-3-one
  参考文献：
  名称：

  Free Radical Methodology for Carbohydrate to Carbocycle Transformations: An Efficient Synthesis of the Tricyclic Dihydrofuran Portion of Azadirachtin

  摘要：

  Iodo lactone 6b, derived from D-galactal, undergoes tin hydride mediated transannular radical cyclization to give the tricyclic lactone 7, which is easily converted into an advanced precursor of the tricyclic dihydrofuran portion of the potent insect antifeedant azadirachtin (1).

  DOI：

  10.1021/jo00097a007