(3R,4R)-tert-butyl-3-(4-(benzyloxy)benzamido)-4-(3,5-bis(benzyloxy)-4-(2-(benzyloxy)-6-(benzyloxycarbonyl)benzoyl)benzoyloxy)azepane-1-carboxylate | 158980-66-6

• 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: (3R,4R)-tert-butyl-3-(4-(benzyloxy)benzamido)-4-(3,5-bis(benzyloxy)-4-(2-(benzyloxy)-6-(benzyloxycarbonyl)benzoyl)benzoyloxy)azepane-1-carboxylate
• 英文别名: tert-butyl (3R,4R)-4-[3,5-bis(phenylmethoxy)-4-(2-phenylmethoxy-6-phenylmethoxycarbonylbenzoyl)benzoyl]oxy-3-[(4-phenylmethoxybenzoyl)amino]azepane-1-carboxylate
• CAS: 158980-66-6
• 化学式: C₆₈H₆₄N₂O₁₂
• 分子量: 1101.26
• InChiKey: IYTXYTVDBRXSBB-WRZFLEQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  82
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  165
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (3R,4R)-tert-butyl-3-(4-(benzyloxy)benzamido)-4-(3,5-bis(benzyloxy)-4-(2-(benzyloxy)-6-(benzyloxycarbonyl)benzoyl)benzoyloxy)azepane-1-carboxylate 在 palladium dihydroxide 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 (-)-Balanol

  摘要：

  (-)-Balanol是一种具有强效蛋白激酶C抑制活性的真菌 metabolite，我们已通过全合成方法成功制备。该合成方法采用了阴离子同系Fries重排策略来构建苯丙酮（benzophenone）部分，同时将叠氮（azepane）部分由(2S,3R)-3-羟基赖氨酸（3-hydroxylysine）获取。

  DOI：

  10.1021/jo00097a014
• 作为产物：
  描述：

  (3R,4R)-3-氨基-4-氮杂环庚醇 在 sodium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3R,4R)-tert-butyl-3-(4-(benzyloxy)benzamido)-4-(3,5-bis(benzyloxy)-4-(2-(benzyloxy)-6-(benzyloxycarbonyl)benzoyl)benzoyloxy)azepane-1-carboxylate
  参考文献：
  名称：

  Total Synthesis of (-)-Balanol

  摘要：

  (-)-Balanol是一种具有强效蛋白激酶C抑制活性的真菌 metabolite，我们已通过全合成方法成功制备。该合成方法采用了阴离子同系Fries重排策略来构建苯丙酮（benzophenone）部分，同时将叠氮（azepane）部分由(2S,3R)-3-羟基赖氨酸（3-hydroxylysine）获取。

  DOI：

  10.1021/jo00097a014

文献信息

• Total Synthesis of (−)-Balanol
  作者：Hideto Miyabe、Mayumi Torieda、Kyoko Inoue、Kazumi Tajiri、Toshiko Kiguchi、Takeaki Naito

  DOI：10.1021/jo980208r

  日期：1998.6.1

  The efficient total synthesis of (-)-balanol, a potent inhibitor of the protein kinase C, is described. (-)-Balanol consists,of a chiral hexahydroazepine-containing fragment and a benzophenone fragment, both of which were prepared via novel synthetic routes. The hexahydroazepine fragment was prepared in racemic form through either Bu3SnH- or SmI2-promoted radical cyclization of oxime ethers 2ab intramolecularly connected with the formyl group. SmI2-promoted radical cyclization of 2b was found to be particularly successful in the selective synthesis of the seven-membered trans-amino alcohol 8b. Preparation of the enantiomerically pure hexahydroazepine-containing fragment was achieved through the enantioselective enzymatic acetylation of racemic alcohol 9, employing the immobilized lipase from Pseudomonas sp. The benzophenone fragment was prepared in short steps through a biomimetic oxidative anthraquinone ring cleavage starting from commercially available natural chrysophanic acid 15c. This reaction proceeded via [4 + 2]-cycloaddition of singlet oxygen to anthracene derivative 17c, followed by Baeyer-Villiger-type rearrangement of the resulting hydroperoxide to afford the benzophenone derivatives 22 and 23.
• 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.
• Total Synthesis of (-)-Balanol
  作者：John W. Lampe、Philip F. Hughes、Christopher K. Biggers、Shelley H. Smith、Hong Hu

  DOI：10.1021/jo00097a014

  日期：1994.9

  (-)-Balanol, a fungal metabolite with potent protein kinase C inhibitory properties, has been prepared in a total synthesis which makes use of an anionic homo-Fries rearrangement approach to the benzophenone subunit and in which the azepane subunit is obtained from (2S,3R)-3-hydroxylysine.

  (-)-Balanol是一种具有强效蛋白激酶C抑制活性的真菌 metabolite，我们已通过全合成方法成功制备。该合成方法采用了阴离子同系Fries重排策略来构建苯丙酮（benzophenone）部分，同时将叠氮（azepane）部分由(2S,3R)-3-羟基赖氨酸（3-hydroxylysine）获取。
• Divergent response of homologous ATP sites to stereospecific ligand fluorination for selectivity enhancement
  作者：Alpesh Ramanlal Patel、Ari Hardianto、Shoba Ranganathan、Fei Liu

  DOI：10.1039/c7ob00129k

  日期：——

  Enhanced selectivity for homologous ATP sites by composite chemical and conformational perturbation by stereospecific fluorination.

  通过立体特异性氟化对同源ATP位点进行复合化学和构象扰动，增强了对同源ATP位点的选择性。