(2R,4E,6E,10S,11S,12E,14S,18E)-4-methyl-2-((R,3E,5E)-4-methyl-6-(3-methylbut-2-enamido)hexa-3,5-dien-2-yl)-20-oxo-11,14-bis((triisopropylsilyl)oxy)oxacycloicosa-4,6,12,18-tetraen-10-yl carbamate | 1191072-52-2

• 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: (2R,4E,6E,10S,11S,12E,14S,18E)-4-methyl-2-((R,3E,5E)-4-methyl-6-(3-methylbut-2-enamido)hexa-3,5-dien-2-yl)-20-oxo-11,14-bis((triisopropylsilyl)oxy)oxacycloicosa-4,6,12,18-tetraen-10-yl carbamate
• CAS: 1191072-52-2
• 化学式: C₅₁H₈₈N₂O₇Si₂
• 分子量: 897.44
• InChiKey: HBMIXJFUYYPYEZ-DMSDYCSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.63
• 重原子数：
  62.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  126.18
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,4E,6E,10S,11S,12E,14S,18E)-4-methyl-2-((R,3E,5E)-4-methyl-6-(3-methylbut-2-enamido)hexa-3,5-dien-2-yl)-20-oxo-11,14-bis((triisopropylsilyl)oxy)oxacycloicosa-4,6,12,18-tetraen-10-yl carbamate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以100%的产率得到(2R,4E,6E,10S,11S,12E,14S,18E)-11,14-dihydroxy-4-methyl-2-{(2R,3E,5E)-4-methyl-6-[(3-methylbut-2-enoyl)amino]hexa-3,5-dien-2-yl}-20-oxooxacycloicosa-4,6,12,18-tetraen-10-yl carbamate
  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：

  N-((R,1E,3E)-5-((2R,4E,6E,10S,11S,12E,14S,18E)-10-hydroxy-4-methyl-20-oxo-11,14-bis((triisopropylsilyl)oxy)oxacycloicosa-4,6,12,18-tetraen-2-yl)-3-methylhexa-1,3-dien-1-yl)-3-methylbut-2-enamide 、 三氯乙酰异氰酸酯 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以40%的产率得到(2R,4E,6E,10S,11S,12E,14S,18E)-4-methyl-2-((R,3E,5E)-4-methyl-6-(3-methylbut-2-enamido)hexa-3,5-dien-2-yl)-20-oxo-11,14-bis((triisopropylsilyl)oxy)oxacycloicosa-4,6,12,18-tetraen-10-yl carbamate
  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