(1S,4S,7S,10S,13S,16S,19S,22S,25R,27S)-19,22-Dibenzyl-10,13-bis-((S)-sec-butyl)-27-hydroxy-7,16-diisobutyl-4-isopropyl-2,5,8,11,14,17,20,23-octaaza-bicyclo[23.2.2]nonacosan-3,6,9,12,15,18,21,24-octaone | 349494-58-2

• 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,4S,7S,10S,13S,16S,19S,22S,25R,27S)-19,22-Dibenzyl-10,13-bis-((S)-sec-butyl)-27-hydroxy-7,16-diisobutyl-4-isopropyl-2,5,8,11,14,17,20,23-octaaza-bicyclo[23.2.2]nonacosan-3,6,9,12,15,18,21,24-octaone
• 英文别名: (1S,4S,7S,10S,13S,16S,19S,22S,25R,27S)-19,22-dibenzyl-10,13-bis[(2S)-butan-2-yl]-27-hydroxy-7,16-bis(2-methylpropyl)-4-propan-2-yl-2,5,8,11,14,17,20,23-octazabicyclo[23.2.2]nonacosane-3,6,9,12,15,18,21,24-octone
• CAS: 349494-58-2
• 化学式: C₅₄H₈₂N₈O₉
• 分子量: 987.293
• InChiKey: IGRGKISQOWJFHY-RWQBAFJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  71
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  253
• 氢给体数：
  9
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S,4S,7S,10S,13S,16S,19S,22S,25R,27S)-19,22-Dibenzyl-10,13-bis-((S)-sec-butyl)-27-hydroxy-7,16-diisobutyl-4-isopropyl-2,5,8,11,14,17,20,23-octaaza-bicyclo[23.2.2]nonacosan-3,6,9,12,15,18,21,24-octaone 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 以45%的产率得到(1S,4S,7S,10S,13S,16S,19S,22S,25R)-19,22-Dibenzyl-10,13-bis-((S)-sec-butyl)-7,16-diisobutyl-4-isopropyl-2,5,8,11,14,17,20,23-octaaza-bicyclo[23.2.2]nonacosane-3,6,9,12,15,18,21,24,27-nonaone
  参考文献：
  名称：

  Stereoisomers of 4-amino-3-hydroxy-1-cyclohexanecarboxylic acid and 4-amino-3-oxo-1-cyclohexanecarboxylic acid as mimetics of a twisted cis-amide bond

  摘要：

  Stereoselective synthesis of the title compounds was performed. The relative configuration of methyl t-4-(tert-butoxycarbonylamino)-c-3-hydroxy-r-1-cyclohexanecarboxylate and methyl trans-4-(tert-butoxycarbonylamino)-3-oxo-r-1-cyclohexanecarboxylate was confirmed by X-ray diffraction methods. Analogues of cyclolinopeptide A (CLA) containing these twisted cis-amide bond mimetics were then synthesised. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00062-3
• 作为产物：
  描述：

  (1R,3S,4S)-4-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-cyclohexanecarboxylic acid 在 4-二甲氨基吡啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 175.0h， 生成 (1S,4S,7S,10S,13S,16S,19S,22S,25R,27S)-19,22-Dibenzyl-10,13-bis-((S)-sec-butyl)-27-hydroxy-7,16-diisobutyl-4-isopropyl-2,5,8,11,14,17,20,23-octaaza-bicyclo[23.2.2]nonacosan-3,6,9,12,15,18,21,24-octaone
  参考文献：
  名称：

  Stereoisomers of 4-amino-3-hydroxy-1-cyclohexanecarboxylic acid and 4-amino-3-oxo-1-cyclohexanecarboxylic acid as mimetics of a twisted cis-amide bond

  摘要：

  Stereoselective synthesis of the title compounds was performed. The relative configuration of methyl t-4-(tert-butoxycarbonylamino)-c-3-hydroxy-r-1-cyclohexanecarboxylate and methyl trans-4-(tert-butoxycarbonylamino)-3-oxo-r-1-cyclohexanecarboxylate was confirmed by X-ray diffraction methods. Analogues of cyclolinopeptide A (CLA) containing these twisted cis-amide bond mimetics were then synthesised. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00062-3