ethyl (E)-3-((1R,2S,3S,E)-2-(2-(benzyloxy)ethyl)-6-(1-((tert-butyldimethylsilyl)oxy)propan-2-ylidene)-3-(methoxymethoxy)-2,3-dimethylcyclohexyl)acrylate | 1021492-05-6

• 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: ethyl (E)-3-((1R,2S,3S,E)-2-(2-(benzyloxy)ethyl)-6-(1-((tert-butyldimethylsilyl)oxy)propan-2-ylidene)-3-(methoxymethoxy)-2,3-dimethylcyclohexyl)acrylate
• CAS: 1021492-05-6
• 化学式: C₃₃H₅₄O₆Si
• 分子量: 574.874
• InChiKey: LXKKOPNOMVPIKZ-KXDJFZJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.85
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 ethyl (E)-3-((1R,2S,3S,E)-2-(2-(benzyloxy)ethyl)-6-(1-((tert-butyldimethylsilyl)oxy)propan-2-ylidene)-3-(methoxymethoxy)-2,3-dimethylcyclohexyl)acrylate 在 碘 、 magnesium 作用下， 反应 2.0h， 以95%的产率得到methyl 3-((1R,2S,3S,E)-2-(2-(benzyloxy)ethyl)-6-(1-((tert-butyldimethylsilyl)oxy)propan-2-ylidene)-3-(methoxymethoxy)-2,3-dimethylcyclohexyl)propanoate
  参考文献：
  名称：

  Enantioselective Synthesis of Iridal, the Parent Molecule of the Iridal Triterpenoid Class

  摘要：

  The monocyclic triterpene iridal 1 (parent molecule) is synthesized by an approach that allows access for several representatives of the iridal family as well as diversely substituted analogues. The success of the proposed synthetic plan depends upon. the effortless stereoselective establishment of the trans C10/C11 dimethyl relationship in B-ring moiety 7 using a domino-based methodology and the higly efficient Miyaura - Suzuki type sp(3) - sp(2) segment coupling 7 and 8, respectively.

  DOI：

  10.1021/ol8005425
• 作为产物：
  描述：

  ethyl (E)-3-[(1R,2S,3S,6E)-6-(1-hydroxypropan-2-ylidene)-3-(methoxymethoxy)-2,3-dimethyl-2-(2-phenylmethoxyethyl)cyclohexyl]prop-2-enoate 、 叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以150 mg的产率得到ethyl (E)-3-((1R,2S,3S,E)-2-(2-(benzyloxy)ethyl)-6-(1-((tert-butyldimethylsilyl)oxy)propan-2-ylidene)-3-(methoxymethoxy)-2,3-dimethylcyclohexyl)acrylate
  参考文献：
  名称：

  Enantioselective Synthesis of Iridal, the Parent Molecule of the Iridal Triterpenoid Class

  摘要：

  The monocyclic triterpene iridal 1 (parent molecule) is synthesized by an approach that allows access for several representatives of the iridal family as well as diversely substituted analogues. The success of the proposed synthetic plan depends upon. the effortless stereoselective establishment of the trans C10/C11 dimethyl relationship in B-ring moiety 7 using a domino-based methodology and the higly efficient Miyaura - Suzuki type sp(3) - sp(2) segment coupling 7 and 8, respectively.

  DOI：

  10.1021/ol8005425