(4E,13E)-(6R,7R,11R,12S,18R)-7-(4-methoxybenzyloxy)-6,11,18-trimethyl-17-methylene-20-((2RS)-tetrahydropyran-2-yloxy)-12-(triisopropylsilanyloxy)icosa-4,13-dien-9-yn-8-one | 1071956-57-4

• 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: (4E,13E)-(6R,7R,11R,12S,18R)-7-(4-methoxybenzyloxy)-6,11,18-trimethyl-17-methylene-20-((2RS)-tetrahydropyran-2-yloxy)-12-(triisopropylsilanyloxy)icosa-4,13-dien-9-yn-8-one
• 英文别名: (4E,6R,7R,11R,12S,13E,18R)-7-[(4-methoxyphenyl)methoxy]-6,11,18-trimethyl-17-methylidene-20-(oxan-2-yloxy)-12-tri(propan-2-yl)silyloxyicosa-4,13-dien-9-yn-8-one
• CAS: 1071956-57-4
• 化学式: C₄₆H₇₄O₆Si
• 分子量: 751.175
• InChiKey: FCHVWZHWHIKMAE-YKMWYCKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  53
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4E,13E)-(6R,7R,11R,12S,18R)-7-(4-methoxybenzyloxy)-6,11,18-trimethyl-17-methylene-20-((2RS)-tetrahydropyran-2-yloxy)-12-(triisopropylsilanyloxy)icosa-4,13-dien-9-yn-8-one 在 Ru[(S,S)-Tsdpen](p-cymene) 作用下， 以 异丙醇 为溶剂， 反应 1.5h， 以96%的产率得到(4E,13E)-(6R,7R,8R,11R,12S,18R)-7-(4-methoxybenzyloxy)-6,11,18-trimethyl-17-methylene-20-((2RS)-tetrahydropyran-2-yloxy)-12-(triisopropylsilanyloxy)icosa-4,13-dien-9-yn-8-ol
  参考文献：
  名称：

  Total Synthesis of Amphidinolide J

  摘要：

  The marine natural product amphidinolide J has been synthesized according to a convergent strategy. The key steps of this synthesis include a B-alkyl Suzuki-Miyaura coupling and the addition of an alkynyllithium reagent to a Weinreb amide to build the C4-C5 and C12-C13 bonds, respectively, and a Yamaguchi macrolactonization.

  DOI：

  10.1021/ol801708x
• 作为产物：
  描述：

  N-methoxy-N-methyl-(E)-(2R,3R)-2-(4-methoxybenzyloxy)-3-methyloct-4-enamide 、 triisopropyl[(E)-(1S,7R)-7-methyl-6-methylene-1-((R)-1-methylprop-2-ynyl)-9-((2RS)-tetrahydropyran-2-yloxy)non-2-enyloxy]silane 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 以147 mg的产率得到(4E,13E)-(6R,7R,11R,12S,18R)-7-(4-methoxybenzyloxy)-6,11,18-trimethyl-17-methylene-20-((2RS)-tetrahydropyran-2-yloxy)-12-(triisopropylsilanyloxy)icosa-4,13-dien-9-yn-8-one
  参考文献：
  名称：

  Total Synthesis of Amphidinolide J

  摘要：

  The marine natural product amphidinolide J has been synthesized according to a convergent strategy. The key steps of this synthesis include a B-alkyl Suzuki-Miyaura coupling and the addition of an alkynyllithium reagent to a Weinreb amide to build the C4-C5 and C12-C13 bonds, respectively, and a Yamaguchi macrolactonization.

  DOI：

  10.1021/ol801708x

文献信息

• Total Synthesis of Amphidinolide J
  作者：Marion Barbazanges、Christophe Meyer、Janine Cossy

  DOI：10.1021/ol801708x

  日期：2008.10.16

  The marine natural product amphidinolide J has been synthesized according to a convergent strategy. The key steps of this synthesis include a B-alkyl Suzuki-Miyaura coupling and the addition of an alkynyllithium reagent to a Weinreb amide to build the C4-C5 and C12-C13 bonds, respectively, and a Yamaguchi macrolactonization.