(1S,4R,5R,6S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-4-hydroxy-2-oxabicyclo[3.2.1]octan-3-one | 158469-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,4R,5R,6S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-4-hydroxy-2-oxabicyclo[3.2.1]octan-3-one
• CAS: 158469-42-2
• 化学式: C₁₆H₃₀O₆Si
• 分子量: 346.496
• InChiKey: JRLSXDNMYOKBFQ-SJHCENCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,4R,5R,6S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-4-hydroxy-2-oxabicyclo[3.2.1]octan-3-one 在 lithium perchlorate 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 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 、 偶氮二异丁腈 、 三正丁基氢锡 、 4-甲基苯磺酸吡啶 、 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] 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 5.0h， 生成 (1S,4R,5R,6S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-4-hydroxy-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

文献信息

• Free Radical Methodology for Carbohydrate to Carbocycle Transformations: An Efficient Synthesis of the Tricyclic Dihydrofuran Portion of Azadirachtin
  作者：Kenneth J. Henry、Bert Fraser-Reid

  DOI：10.1021/jo00097a007

  日期：1994.9

  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).