(5R,8S,10R,11R)-tert-butyl 13-benzyl-4-(benzyloxy)-5-(hydroxymethyl)-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepino[1,2-b]isoquinoline-10-carboxylate | 1448531-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (5R,8S,10R,11R)-tert-butyl 13-benzyl-4-(benzyloxy)-5-(hydroxymethyl)-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepino[1,2-b]isoquinoline-10-carboxylate
• 英文别名: tert-butyl (1R,10R,13S,15R)-16-benzyl-10-(hydroxymethyl)-7-methoxy-6-methyl-12-oxo-8-phenylmethoxy-11,16-diazatetracyclo[11.2.1.02,11.04,9]hexadeca-2,4(9),5,7-tetraene-15-carboxylate
• CAS: 1448531-08-5
• 化学式: C₃₆H₄₀N₂O₆
• 分子量: 596.723
• InChiKey: PFYIBPFMLHOLDO-BTURHGITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  88.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5R,8S,10R,11R)-tert-butyl 13-benzyl-4-(benzyloxy)-5-(hydroxymethyl)-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepino[1,2-b]isoquinoline-10-carboxylate 在 palladium on activated charcoal 、 氢气 作用下， 以 溶剂黄146 为溶剂， 以92%的产率得到(5R,8R,10S,11R)-tert-butyl 4-hydroxy-5-(hydroxymethyl)-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepino[1,2-b]isoquinoline-10-carboxylate
  参考文献：
  名称：

  Synthetic studies on lemonomycin: construction of the tetracyclic core

  摘要：

  A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.05.009
• 作为产物：
  描述：

  (8S,10R,11R)-tert-butyl 13-benzyl-4-(benzyloxy)-5-formyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepino[1,2-b]isoquinoline-10-carboxylate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以30%的产率得到(5S,8S,10R,11R)-tert-butyl 13-benzyl-4-(benzyloxy)-5-(hydroxymethyl)-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepino[1,2-b]isoquinoline-10-carboxylate
  参考文献：
  名称：

  Synthetic studies on lemonomycin: construction of the tetracyclic core

  摘要：

  A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.05.009