(1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate | 1448530-96-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate
• 英文别名: ethyl (1S,3S)-8-acetyloxy-2-[2-[benzyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetyl]-3-formyl-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-1-carboxylate
• CAS: 1448530-96-8
• 化学式: C₃₁H₃₈N₂O₉
• 分子量: 582.651
• InChiKey: SAHBDLAFBPXKFV-OZXSUGGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  丙烯酸叔丁酯 、 (1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate 在 2,2,6,6-四甲基哌啶氧化物 、 三氟乙酸 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以41%的产率得到(5S,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate
  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：

  (1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)acetyl)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 (1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-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