(3R,3aR,5R,6R,8S,9S,9aR)-6-methyl-9-{(1R)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-6,8-bis[(triethylsilyl)oxy]hexahydro-2H-3,5-ethanofuro[3,2-b]oxocine-3,9(3aH)-diol | 1006701-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3R,3aR,5R,6R,8S,9S,9aR)-6-methyl-9-{(1R)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-6,8-bis[(triethylsilyl)oxy]hexahydro-2H-3,5-ethanofuro[3,2-b]oxocine-3,9(3aH)-diol
• 英文别名: (1R,4R,7R,8R,10S,11S,12R)-8-methyl-8,10-bis(triethylsilyloxy)-11-[(2R)-1-tri(propan-2-yl)silyloxypropan-2-yl]-2,13-dioxatricyclo[5.4.2.04,12]tridecane-4,11-diol
• CAS: 1006701-74-1
• 化学式: C₃₆H₇₄O₇Si₃
• 分子量: 703.236
• InChiKey: QGINIRAGQGNVQU-ZRTAFWODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,3aR,5R,6R,8S,9S,9aR)-6-methyl-9-{(1R)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-6,8-bis[(triethylsilyl)oxy]hexahydro-2H-3,5-ethanofuro[3,2-b]oxocine-3,9(3aH)-diol 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 5.0h， 以75%的产率得到(3R,3aR,5R,6R,8S,9S,9aR)-6-methyl-9-{(1R)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-6,8-bis[(triethylsilyl)oxy]hexahydro-3,5-(ethanylylidene)furo[3,2-b]oxocine-3,9(2H)-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
• 作为产物：
  描述：

  (1R,2S,4S,5S,7R,8R,11R)-11-(hydroxymethyl)-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-ol 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以75%的产率得到(3R,3aR,5R,6R,8S,9S,9aR)-6-methyl-9-{(1R)-1-methyl-2-[(triisopropylsilyl)oxy]ethyl}-6,8-bis[(triethylsilyl)oxy]hexahydro-2H-3,5-ethanofuro[3,2-b]oxocine-3,9(3aH)-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