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 | 1191072-33-9

• 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 (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
• CAS: 1191072-33-9
• 化学式: C₃₀H₄₈O₇Si
• 分子量: 548.792
• InChiKey: QEIGQPPTXSIEAE-AONNKGDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 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]-2-[(4-methoxyphenyl)methoxy]-3-tri(propan-2-yl)silyloxypent-4-enoate 在 Rh/Al₂O₃ 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 4.0h， 生成
  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 (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

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.