benzyl (2S)-2-[[4-[2-[[5-[[(1S)-1-benzyloxycarbonyl-3-methyl-butyl]carbamoyl]-1H-imidazole-4-carbonyl]-ethyl-amino]ethyl-ethyl-carbamoyl]-1H-imidazole-5-carbonyl]amino]-4-methyl-pentanoate | 623576-16-9

• 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: benzyl (2S)-2-[[4-[2-[[5-[[(1S)-1-benzyloxycarbonyl-3-methyl-butyl]carbamoyl]-1H-imidazole-4-carbonyl]-ethyl-amino]ethyl-ethyl-carbamoyl]-1H-imidazole-5-carbonyl]amino]-4-methyl-pentanoate
• 英文别名: benzyl (2S)-2-[[5-[ethyl-[2-[ethyl-[4-[[(2S)-4-methyl-1-oxo-1-phenylmethoxypentan-2-yl]carbamoyl]-1H-imidazole-5-carbonyl]amino]ethyl]carbamoyl]-1H-imidazole-4-carbonyl]amino]-4-methylpentanoate
• CAS: 623576-16-9
• 化学式: C₄₂H₅₄N₈O₈
• 分子量: 798.94
• InChiKey: WMOPZIBLFAFMQU-ACHIHNKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  58
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  209
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl (2S)-2-[[4-[2-[[5-[[(1S)-1-benzyloxycarbonyl-3-methyl-butyl]carbamoyl]-1H-imidazole-4-carbonyl]-ethyl-amino]ethyl-ethyl-carbamoyl]-1H-imidazole-5-carbonyl]amino]-4-methyl-pentanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到(2S)-2-[[5-[2-[[4-[[(1S)-1-carboxy-3-methylbutyl]carbamoyl]-1H-imidazole-5-carbonyl]-ethylamino]ethyl-ethylcarbamoyl]-1H-imidazole-4-carbonyl]amino]-4-methylpentanoic acid
  参考文献：
  名称：

  Synthesis of Symmetric Bis(imidazole-4,5-dicarboxamides) Substituted with Amino Acids

  摘要：

  A series of symmetric bis(imidazole-4,5-dicarboxamides) (bis-I45DCs) were prepared with amino acid esters and a variety of linker groups. The critical pyrazine intermediates, substituted with amino acid esters, were synthesized by stoichiometric control of the amino acid ester, even though primary alkanamines, in comparison, generally offer less selectivity for this reaction. Diamines are added to subsequently react with and open the remaining acyl imidazole bonds in the pyrazine intermediates and thereby yield the bis-I45DCs.

  DOI：

  10.1021/jo049045z
• 作为产物：
  描述：

  L-亮氨酸苄酯盐酸盐(1:1) 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 benzyl (2S)-2-[[4-[2-[[5-[[(1S)-1-benzyloxycarbonyl-3-methyl-butyl]carbamoyl]-1H-imidazole-4-carbonyl]-ethyl-amino]ethyl-ethyl-carbamoyl]-1H-imidazole-5-carbonyl]amino]-4-methyl-pentanoate
  参考文献：
  名称：

  Synthesis of Symmetric Bis(imidazole-4,5-dicarboxamides) Substituted with Amino Acids

  摘要：

  A series of symmetric bis(imidazole-4,5-dicarboxamides) (bis-I45DCs) were prepared with amino acid esters and a variety of linker groups. The critical pyrazine intermediates, substituted with amino acid esters, were synthesized by stoichiometric control of the amino acid ester, even though primary alkanamines, in comparison, generally offer less selectivity for this reaction. Diamines are added to subsequently react with and open the remaining acyl imidazole bonds in the pyrazine intermediates and thereby yield the bis-I45DCs.

  DOI：

  10.1021/jo049045z

文献信息

• Synthesis of Symmetric Bis(imidazole-4,5-dicarboxamides) Substituted with Amino Acids
  作者：Alexander V. Wiznycia、Jeremy R. Rush、Paul W. Baures

  DOI：10.1021/jo049045z

  日期：2004.11.1

  A series of symmetric bis(imidazole-4,5-dicarboxamides) (bis-I45DCs) were prepared with amino acid esters and a variety of linker groups. The critical pyrazine intermediates, substituted with amino acid esters, were synthesized by stoichiometric control of the amino acid ester, even though primary alkanamines, in comparison, generally offer less selectivity for this reaction. Diamines are added to subsequently react with and open the remaining acyl imidazole bonds in the pyrazine intermediates and thereby yield the bis-I45DCs.