methyl (1R,2R,4S,5S,6S,7R,8S)-5,6,8-trihydroxy-2-methyl-5-{(1R)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-2,4-bis[(triethylsilyl)oxy]-11-oxabicyclo[5.3.1]undecane-8-carboxylate | 1006701-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: methyl (1R,2R,4S,5S,6S,7R,8S)-5,6,8-trihydroxy-2-methyl-5-{(1R)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-2,4-bis[(triethylsilyl)oxy]-11-oxabicyclo[5.3.1]undecane-8-carboxylate
• 英文别名: methyl (1R,2R,4S,5S,6S,7R,8S)-5,6,8-trihydroxy-2-methyl-2,4-bis(triethylsilyloxy)-5-[(2R)-1-tri(propan-2-yl)silyloxypropan-2-yl]-11-oxabicyclo[5.3.1]undecane-8-carboxylate
• CAS: 1006701-71-8
• 化学式: C₃₇H₇₆O₉Si₃
• 分子量: 749.262
• InChiKey: ZJNIQLPWJQYMQD-WLSGVQNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.93
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (1R,2R,4S,5S,6S,7R,8S)-5,6,8-trihydroxy-2-methyl-5-{(1R)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-2,4-bis[(triethylsilyl)oxy]-11-oxabicyclo[5.3.1]undecane-8-carboxylate 在 potassium trimethylsilonate 、 盐酸 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以61%的产率得到(3S,3aR,5R,6R,8S,9S,9aS)-3,9-dihydroxy-6-methyl-9-{(1R)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-6,8-bis[(triethylsilyl)oxy]octahydro-2H-3,5-ethanofuro[3,2-b]oxocin-2-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：

  methyl (1R,2R,4S,5Z,7R,8S)-8-hydroxy-2-methyl-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-2,4-bis[(triethylsilyl)oxy]-11-oxabicyclo[5.3.1]undec-5-en-8-carboxylate 在 四氧化锇 作用下， 以 吡啶 、 水 、 丙酮 为溶剂， 反应 3.0h， 以84%的产率得到methyl (1R,2R,4S,5S,6S,7R,8S)-5,6,8-trihydroxy-2-methyl-5-{(1R)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-2,4-bis[(triethylsilyl)oxy]-11-oxabicyclo[5.3.1]undecane-8-carboxylate
  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