methyl (2E,7S,8E,10S,11S)-11-[(4-methoxybenzyl)oxy]-7,10-bis[(tri(propan-2-yl)silyl)oxy]trideca-2,8,12-trienoate | 1191072-26-0

• 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: methyl (2E,7S,8E,10S,11S)-11-[(4-methoxybenzyl)oxy]-7,10-bis[(tri(propan-2-yl)silyl)oxy]trideca-2,8,12-trienoate
• 英文别名: methyl (2E,7S,8E,10S,11S)-11-[(4-methoxyphenyl)methoxy]-7,10-bis[tri(propan-2-yl)silyloxy]trideca-2,8,12-trienoate
• CAS: 1191072-26-0
• 化学式: C₄₀H₇₀O₆Si₂
• 分子量: 703.163
• InChiKey: XNINMEYQDYXTTG-CYAHSSEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.34
• 重原子数：
  48
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  tert-butyl (2E,4E,6R,7R,9E,11E)-7-hydroxy-12-iodo-4,6,9-trimethyldodeca-2,4,9,11-tetraenoate 、 methyl (2E,7S,8E,10S,11S)-11-[(4-methoxybenzyl)oxy]-7,10-bis[(tri(propan-2-yl)silyl)oxy]trideca-2,8,12-trienoate 在 9-硼双环[3.3.1]壬烷 、 水 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三苯胂 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以77%的产率得到1-tert-butyl 25-methyl (2E,4E,6R,7R,9E,11E,15S,16S,17E,19S,23E)-7-hydroxy-15-[(4-methoxybenzyl)oxy]-4,6,9-trimethyl-16,19-bis[(tri(propan-2-yl)silyl)oxy]pentacosa-2,4,9,11,17,23-hexaenedioate
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Palmerolide A via Organoboron Methodology

  摘要：

  A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl4-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could the way to the design of simplified analogues of palmerolide.

  DOI：

  10.1021/ja906429c
• 作为产物：
  描述：

  methyl (2E,7S,8E,10S,11S)-7-hydroxy-11-[(4-methoxybenzyl)oxy]-10-[(tri(propan-2-yl)silyl)oxy]trideca-2,8,12-trienoate 、 三异丙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到methyl (2E,7S,8E,10S,11S)-11-[(4-methoxybenzyl)oxy]-7,10-bis[(tri(propan-2-yl)silyl)oxy]trideca-2,8,12-trienoate
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Palmerolide A via Organoboron Methodology

  摘要：

  A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl4-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could the way to the design of simplified analogues of palmerolide.

  DOI：

  10.1021/ja906429c

文献信息

• Catalytic Asymmetric Synthesis of Palmerolide A via Organoboron Methodology
  作者：Marlin Penner、Vivek Rauniyar、Ludwig T. Kaspar、Dennis G. Hall

  DOI：10.1021/ja906429c

  日期：2009.10.14

  A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl4-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could the way to the design of simplified analogues of palmerolide.