(2E)-1-[(2S,6R)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol | 1191072-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2E)-1-[(2S,6R)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol
• 英文别名: (E,1S)-1-[(2R,6S)-2-ethoxy-3,6-dihydro-2H-pyran-6-yl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol
• CAS: 1191072-31-7
• 化学式: C₁₆H₂₇BO₅
• 分子量: 310.198
• InChiKey: MTYASPLKWPXIKU-FLLGMSFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-1-[(2S,6R)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol 、 (4-甲氧基苄氧基)乙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(2E)-1-[(2S,6R)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl [(4-methoxybenzyl)oxy]acetate
  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：

  乙烯基乙醚 、 3-boronoacrolein pinacolate 在 barium(II) oxide 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到(2E)-1-[(2S,6R)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol
  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.