(1R,2S,4S,5S,7R,8R,11S)-11-hydroxy-7-methyl-5,7-bis(triethylsilyloxy)-4-[(2R)-1-tri(propan-2-yl)silyloxypropan-2-yl]-3,12-dioxatricyclo[6.3.1.02,4]dodecane-11-carboxylic acid | 1006701-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,2S,4S,5S,7R,8R,11S)-11-hydroxy-7-methyl-5,7-bis(triethylsilyloxy)-4-[(2R)-1-tri(propan-2-yl)silyloxypropan-2-yl]-3,12-dioxatricyclo[6.3.1.02,4]dodecane-11-carboxylic acid
• CAS: 1006701-76-3
• 化学式: C₃₆H₇₂O₈Si₃
• 分子量: 717.219
• InChiKey: AOEZGXBLYNTUMU-IYJIBUMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.89
• 重原子数：
  47
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S,5S,7R,8R,11S)-11-hydroxy-7-methyl-5,7-bis(triethylsilyloxy)-4-[(2R)-1-tri(propan-2-yl)silyloxypropan-2-yl]-3,12-dioxatricyclo[6.3.1.02,4]dodecane-11-carboxylic acid 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以27 mg的产率得到(1R,2S,4S,5S,7R,8R)-7-methyl-4-{(1R)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-5,7-bis[(triethylsilyl)oxy]-3,12-dioxatricyclo[6.3.1.0^2,4]dodecan-11-one
  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,2S,4S,5S,7R,8R,11S)-11-hydroxy-7-methyl-5,7-bis(triethylsilyloxy)-4-[(2R)-1-tri(propan-2-yl)silyloxypropan-2-yl]-3,12-dioxatricyclo[6.3.1.02,4]dodecane-11-carbaldehyde 在 sodium chlorite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.25h， 生成 (1R,2S,4S,5S,7R,8R,11S)-11-hydroxy-7-methyl-5,7-bis(triethylsilyloxy)-4-[(2R)-1-tri(propan-2-yl)silyloxypropan-2-yl]-3,12-dioxatricyclo[6.3.1.02,4]dodecane-11-carboxylic acid
  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