methyl (E,2R,3S)-5-[(2R,6S)-2-ethoxy-3,6-dihydro-2H-pyran-6-yl]-3-hydroxy-2-[(4-methoxyphenyl)methoxy]pent-4-enoate | 1191072-32-8

• 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: methyl (E,2R,3S)-5-[(2R,6S)-2-ethoxy-3,6-dihydro-2H-pyran-6-yl]-3-hydroxy-2-[(4-methoxyphenyl)methoxy]pent-4-enoate
• CAS: 1191072-32-8
• 化学式: C₂₁H₂₈O₇
• 分子量: 392.449
• InChiKey: HXRZDOZZQYZKMY-TZGFRYPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (E,2R,3S)-5-[(2R,6S)-2-ethoxy-3,6-dihydro-2H-pyran-6-yl]-3-hydroxy-2-[(4-methoxyphenyl)methoxy]pent-4-enoate 、 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94%的产率得到methyl (E,2R,3S)-5-[(2R,6S)-2-ethoxy-3,6-dihydro-2H-pyran-6-yl]-2-[(4-methoxyphenyl)methoxy]-3-tri(propan-2-yl)silyloxypent-4-enoate
  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：

  重氮甲烷 、 以 乙醇 、 二氯甲烷 为溶剂， 以1.36 g的产率得到methyl (E,2R,3S)-5-[(2R,6S)-2-ethoxy-3,6-dihydro-2H-pyran-6-yl]-3-hydroxy-2-[(4-methoxyphenyl)methoxy]pent-4-enoate
  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