3,5-Bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester

• 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: 3,5-Bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester
• 英文别名: [(3R,4R)-1-benzyl-3-[(4-phenylmethoxybenzoyl)amino]azepan-4-yl] 3,5-bis(phenylmethoxy)-4-(2-phenylmethoxy-6-phenylmethoxycarbonylbenzoyl)benzoate
• 化学式: C₇₀H₆₂N₂O₁₀
• 分子量: 1091.27
• InChiKey: QMBDZUAFICQEOK-GTOSQJSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  82
• 可旋转键数：
  25
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,5-Bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester 在 palladium hydroxide - carbon 氢气 、 三氟乙酸 作用下， 生成 4-(2-羧基-6-羟基苯甲酰基)-3,5-二羟基-苯甲酸 (3R,4R)-六氢-3-[(4-羟基苯甲酰基)氨基]-1H-氮杂卓-4-基酯
  参考文献：
  名称：

  Total Synthesis of (−)- and (+)-Balanol¹

  摘要：

  Two total syntheses of the potent protein kinase C inhibitory fungal metabolite balanol are described. In the first approach, the core aminohydroxyazepane subunit was prepared in racemic form by stereospecific functionalization of N-benzyl-epsilon-caprolactam. Resolution prior to coupling to the benzophenone subunit provided access to both enantiomers of balanol. In the second approach, an efficient silicon-mediated cyclization of(2S,3R)-3-hydroxylysine followed by reduction provided the azepane subunit in enantiomerically pure form. The sterically congested benzophenone subunit was assembled from two highly substituted aromatic precursors by way of an anionic home-Fries rearrangement.

  DOI：

  10.1021/jo952280k
• 作为产物：
  描述：

  己内酰胺 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 四氧化锇 、 lithium aluminium tetrahydride 、 sodium azide 、 草酰氯 、 三氟甲磺酸酐 、 三氟化硼乙醚 、 水 、 双氧水 、 苄基三甲基溴化铵 、 sodium hydride 、 sodium carbonate 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二甲基甲酰胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 丙酮 、 paraffin 、 叔丁醇 为溶剂， 反应 105.5h， 生成 3,5-Bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester
  参考文献：
  名称：

  Total Synthesis of (−)- and (+)-Balanol¹

  摘要：

  Two total syntheses of the potent protein kinase C inhibitory fungal metabolite balanol are described. In the first approach, the core aminohydroxyazepane subunit was prepared in racemic form by stereospecific functionalization of N-benzyl-epsilon-caprolactam. Resolution prior to coupling to the benzophenone subunit provided access to both enantiomers of balanol. In the second approach, an efficient silicon-mediated cyclization of(2S,3R)-3-hydroxylysine followed by reduction provided the azepane subunit in enantiomerically pure form. The sterically congested benzophenone subunit was assembled from two highly substituted aromatic precursors by way of an anionic home-Fries rearrangement.

  DOI：

  10.1021/jo952280k

文献信息

• Total Synthesis of (−)- and (+)-Balanol¹
  作者：John W. Lampe、Philip F. Hughes、Christopher K. Biggers、Shelley H. Smith、Hong Hu

  DOI：10.1021/jo952280k

  日期：1996.1.1

  Two total syntheses of the potent protein kinase C inhibitory fungal metabolite balanol are described. In the first approach, the core aminohydroxyazepane subunit was prepared in racemic form by stereospecific functionalization of N-benzyl-epsilon-caprolactam. Resolution prior to coupling to the benzophenone subunit provided access to both enantiomers of balanol. In the second approach, an efficient silicon-mediated cyclization of(2S,3R)-3-hydroxylysine followed by reduction provided the azepane subunit in enantiomerically pure form. The sterically congested benzophenone subunit was assembled from two highly substituted aromatic precursors by way of an anionic home-Fries rearrangement.