(2S)-2-[[(2S,3S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(1R,3S,4S)-4-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-hydroxycyclohexanecarbonyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoic acid | 349494-54-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (2S)-2-[[(2S,3S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(1R,3S,4S)-4-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-hydroxycyclohexanecarbonyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoic acid
• CAS: 349494-54-8
• 化学式: C₅₄H₈₄N₈O₁₀
• 分子量: 1005.31
• InChiKey: XMDBSLUIOHDEBK-RWQBAFJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  72
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  287
• 氢给体数：
  10
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S)-2-[[(2S,3S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(1R,3S,4S)-4-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-hydroxycyclohexanecarbonyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoic acid 在 4-二甲氨基吡啶 、 重铬酸吡啶 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 214.0h， 生成 (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 、 alkaline earth salt of/the/ methylsulfuric acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 2,3-二巯基丁二酸 、 间甲酚 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (2S)-2-[[(2S,3S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(1R,3S,4S)-4-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-hydroxycyclohexanecarbonyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoic acid
  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