ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octanoate | 1312759-11-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octanoate
• 英文别名: ethyl (6S)-6-[tert-butyl(diphenyl)silyl]oxy-6-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexanoate
• CAS: 1312759-11-7
• 化学式: C₃₂H₄₆O₅Si
• 分子量: 538.8
• InChiKey: JKWBDDOLCSLEAX-URLMMPGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octanoate 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四丁基氟化铵 、 水 、 三氟乙酸 、 sodium iodide 、 potassium hydroxide 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 88.0h， 生成 (6S,7E,9R,10S)-6,9,10-trihydroxyoctadec-7-enoic acid
  参考文献：
  名称：

  First asymmetric synthesis of the oxylipin, (6S,9R,10S)-6,9,10-trihydroxyoctadeca-7E-enoic acid

  摘要：

  A brief and facile synthesis of the title compound has been developed using cyclohexylideneglyceraldehyde as a chiral template. The key steps in the synthesis were: (i) two highly diastereoselective organometallic addition reactions to the aldehyde to furnish the required synthons with the appropriate stereogenic centers, and (ii) their cross metathesis to give the E-olefin geometry of the target compound. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.008
• 作为产物：
  描述：

  1(S)-[(2R)-1,4-dioxaspiro[4.5]decanyl]-3-buten-1-ol 在 咪唑 、 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 palladium 10% on activated carbon 、 氢气 、 sodium acetate 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 71.25h， 生成 ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octanoate
  参考文献：
  名称：

  First asymmetric synthesis of the oxylipin, (6S,9R,10S)-6,9,10-trihydroxyoctadeca-7E-enoic acid

  摘要：

  A brief and facile synthesis of the title compound has been developed using cyclohexylideneglyceraldehyde as a chiral template. The key steps in the synthesis were: (i) two highly diastereoselective organometallic addition reactions to the aldehyde to furnish the required synthons with the appropriate stereogenic centers, and (ii) their cross metathesis to give the E-olefin geometry of the target compound. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.008

文献信息

• First asymmetric synthesis of the oxylipin, (6S,9R,10S)-6,9,10-trihydroxyoctadeca-7E-enoic acid
  作者：Sucheta Chatterjee、Seema V. Kanojia、Subrata Chattopadhyay、Anubha Sharma

  DOI：10.1016/j.tetasy.2011.02.008

  日期：2011.2

  A brief and facile synthesis of the title compound has been developed using cyclohexylideneglyceraldehyde as a chiral template. The key steps in the synthesis were: (i) two highly diastereoselective organometallic addition reactions to the aldehyde to furnish the required synthons with the appropriate stereogenic centers, and (ii) their cross metathesis to give the E-olefin geometry of the target compound. (C) 2011 Elsevier Ltd. All rights reserved.