(1R,2R,4S,5Z,7R)-2-methyl-8-methylene-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-11-oxabicyclo[5.3.1]undec-5-ene-2,4-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,4S,5Z,7R)-2-methyl-8-methylene-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-11-oxabicyclo[5.3.1]undec-5-ene-2,4-diol
• 英文别名: (1R,2R,4S,5Z,7R)-2-methyl-8-methylidene-5-[(2S)-1-tri(propan-2-yl)silyloxypropan-2-yl]-11-oxabicyclo[5.3.1]undec-5-ene-2,4-diol
• 化学式: C₂₄H₄₄O₄Si
• 分子量: 424.696
• InChiKey: AGTGANXREAAVNZ-PQSDKYPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S,5Z,7R)-2-methyl-8-methylene-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-11-oxabicyclo[5.3.1]undec-5-ene-2,4-diol 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以98%的产率得到(1R,2R,4S,5Z,7R)-2-methyl-8-methylene-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-2,4-bis(triethylsilyloxy)-11-oxabicyclo[5.3.1]undec-5-ene
  参考文献：
  名称：

  Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid

  摘要：

  [GRAPHICS]The tricyclic core of the plant-derived sesquiterpene natural product neoliacinic acid was synthesized using a novel synthetic strategy. The pivotal synthetic transformations are construction of the key bicyclic ether-bridged intermediate by sequential deployment of metal carbenoid C-H insertion and ylide-forming reactions and installation of the lactone portion of neoliacinic acid by an acid-catalyzed intramolecular ring-opening reaction of an epoxide with a carboxylic acid.

  DOI：

  10.1021/jo702111u
• 作为产物：
  描述：

  (1R,3S,5S,7R,8R)-7-methyl-11-methylene-3-{(1R)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-4,12-dioxatricyclo[6.3.1.0^3,5]dodec-7-yl acetate 在 aluminum isopropoxide 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以60%的产率得到(1R,2R,4S,5Z,7R)-2-methyl-8-methylene-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-11-oxabicyclo[5.3.1]undec-5-ene-2,4-diol
  参考文献：
  名称：

  Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid

  摘要：

  [GRAPHICS]The tricyclic core of the plant-derived sesquiterpene natural product neoliacinic acid was synthesized using a novel synthetic strategy. The pivotal synthetic transformations are construction of the key bicyclic ether-bridged intermediate by sequential deployment of metal carbenoid C-H insertion and ylide-forming reactions and installation of the lactone portion of neoliacinic acid by an acid-catalyzed intramolecular ring-opening reaction of an epoxide with a carboxylic acid.

  DOI：

  10.1021/jo702111u

文献信息

• Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid
  作者：J. Stephen Clark、Carl A. Baxter、Alexander G. Dossetter、Stéphane Poigny、José L. Castro、William G. Whittingham

  DOI：10.1021/jo702111u

  日期：2008.2.1

  [GRAPHICS]The tricyclic core of the plant-derived sesquiterpene natural product neoliacinic acid was synthesized using a novel synthetic strategy. The pivotal synthetic transformations are construction of the key bicyclic ether-bridged intermediate by sequential deployment of metal carbenoid C-H insertion and ylide-forming reactions and installation of the lactone portion of neoliacinic acid by an acid-catalyzed intramolecular ring-opening reaction of an epoxide with a carboxylic acid.