[(Z,3S,5S,7R,10R)-10-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-(1,3-dithian-2-yl)-3-hydroxy-7-[(4-methoxyphenyl)methoxy]-2,8-dimethyldodec-8-en-5-yl] propanoate | 1092070-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(Z,3S,5S,7R,10R)-10-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-(1,3-dithian-2-yl)-3-hydroxy-7-[(4-methoxyphenyl)methoxy]-2,8-dimethyldodec-8-en-5-yl] propanoate
• CAS: 1092070-67-1
• 化学式: C₄₆H₆₆O₆S₂Si
• 分子量: 807.244
• InChiKey: LJABKWHBZQRSHN-NALVRRQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.81
• 重原子数：
  55
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(Z,3S,5S,7R,10R)-10-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-(1,3-dithian-2-yl)-3-hydroxy-7-[(4-methoxyphenyl)methoxy]-2,8-dimethyldodec-8-en-5-yl] propanoate 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.8h， 以99%的产率得到
  参考文献：
  名称：

  Total Synthesis of (−)-2-epi-Peloruside A

  摘要：

  A convergent synthesis of (-)-2-epi-peloruside A has been achieved. Highlights include implementation of multicomponent type I anion relay chemistry (ARC) to unite 2-TBS-1,3-dithiane with two epoxides to construct the eastern hemisphere, a late-stage dithiane union to secure the complete, fully functionalized carbon backbone, and Yamaguchi macrolactonization, which led to (-)-2-epi-peloruside A via an unexpected epimerization at C(2).

  DOI：

  10.1021/ol8019132
• 作为产物：
  描述：

  (Z,5R,7R,10R)-10-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-(1,3-dithian-2-yl)-5-hydroxy-7-[(4-methoxyphenyl)methoxy]-2,8-dimethyldodec-8-en-3-one 、 丙醛 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 以97%的产率得到[(Z,3S,5S,7R,10R)-10-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-(1,3-dithian-2-yl)-3-hydroxy-7-[(4-methoxyphenyl)methoxy]-2,8-dimethyldodec-8-en-5-yl] propanoate
  参考文献：
  名称：

  Total Synthesis of (−)-2-epi-Peloruside A

  摘要：

  A convergent synthesis of (-)-2-epi-peloruside A has been achieved. Highlights include implementation of multicomponent type I anion relay chemistry (ARC) to unite 2-TBS-1,3-dithiane with two epoxides to construct the eastern hemisphere, a late-stage dithiane union to secure the complete, fully functionalized carbon backbone, and Yamaguchi macrolactonization, which led to (-)-2-epi-peloruside A via an unexpected epimerization at C(2).

  DOI：

  10.1021/ol8019132

文献信息

• Total Synthesis of (−)-2-<i>epi</i>-Peloruside A
  作者：Amos B. Smith、Jason M. Cox、Noriyuki Furuichi、Craig S. Kenesky、Junying Zheng、Onur Atasoylu、William M. Wuest

  DOI：10.1021/ol8019132

  日期：2008.12.18

  A convergent synthesis of (-)-2-epi-peloruside A has been achieved. Highlights include implementation of multicomponent type I anion relay chemistry (ARC) to unite 2-TBS-1,3-dithiane with two epoxides to construct the eastern hemisphere, a late-stage dithiane union to secure the complete, fully functionalized carbon backbone, and Yamaguchi macrolactonization, which led to (-)-2-epi-peloruside A via an unexpected epimerization at C(2).