(2E,4E,6R)-6-{(2R,4E,6E,10S,11S,12E,14S,18E)-10-[(4-methoxybenzyl)oxy]-4-methyl-20-oxo-11,14-bis[(tri(propan-2-yl)silyl)oxy]oxacycloicosa-4,6,12,18-tetraen-2-yl}-4-methylhepta-2,4-dienoic acid | 1191072-49-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (2E,4E,6R)-6-{(2R,4E,6E,10S,11S,12E,14S,18E)-10-[(4-methoxybenzyl)oxy]-4-methyl-20-oxo-11,14-bis[(tri(propan-2-yl)silyl)oxy]oxacycloicosa-4,6,12,18-tetraen-2-yl}-4-methylhepta-2,4-dienoic acid
• 英文别名: (2E,4E,6R)-6-[(2R,4E,6E,10S,11S,12E,14S,18E)-10-[(4-methoxyphenyl)methoxy]-4-methyl-20-oxo-11,14-bis[tri(propan-2-yl)silyloxy]-1-oxacycloicosa-4,6,12,18-tetraen-2-yl]-4-methylhepta-2,4-dienoic acid
• CAS: 1191072-49-7
• 化学式: C₅₄H₈₈O₈Si₂
• 分子量: 921.459
• InChiKey: XQQSNUJWIPGADZ-ROKQHBLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.81
• 重原子数：
  64
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2E,4E,6R)-6-{(2R,4E,6E,10S,11S,12E,14S,18E)-10-[(4-methoxybenzyl)oxy]-4-methyl-20-oxo-11,14-bis[(tri(propan-2-yl)silyl)oxy]oxacycloicosa-4,6,12,18-tetraen-2-yl}-4-methylhepta-2,4-dienoic acid 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 苯 为溶剂， 反应 5.0h， 以88%的产率得到(2E,4E,6R)-6-{(2R,4E,6E,10S,11S,12E,14S,18E)-10-[(4-methoxybenzyl)oxy]-4-methyl-20-oxo-11,14-bis[(tri(propan-2-yl)silyl)oxy]oxacycloicosa-4,6,12,18-tetraen-2-yl}-4-methylhepta-2,4-dienoyl azide
  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：

  tert-butyl (2E,4E,6R)-6-{(2R,4E,6E,10S,11S,12E,14S,18E)-10-[(4-methoxybenzyl)oxy]-4-methyl-20-oxo-11,14-bis[(tri(propan-2-yl)silyl)oxy]oxacycloicosa-4,6,12,18-tetraen-2-yl}-4-methylhepta-2,4-dienoate 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到(2E,4E,6R)-6-{(2R,4E,6E,10S,11S,12E,14S,18E)-10-[(4-methoxybenzyl)oxy]-4-methyl-20-oxo-11,14-bis[(tri(propan-2-yl)silyl)oxy]oxacycloicosa-4,6,12,18-tetraen-2-yl}-4-methylhepta-2,4-dienoic acid
  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.