(S)-methyl 2-((benzyloxycarbonyl)(methyl)amino)-3-(1-(5-(2-(tertbutoxycarbonylamino)ethyl)-2-(methoxymethoxy)phenyl)-1H-imidazol-4-yl)propanoate | 1192262-31-9

• 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: (S)-methyl 2-((benzyloxycarbonyl)(methyl)amino)-3-(1-(5-(2-(tertbutoxycarbonylamino)ethyl)-2-(methoxymethoxy)phenyl)-1H-imidazol-4-yl)propanoate
• 英文别名: methyl (2S)-3-[1-[2-(methoxymethoxy)-5-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]phenyl]imidazol-4-yl]-2-[methyl(phenylmethoxycarbonyl)amino]propanoate
• CAS: 1192262-31-9
• 化学式: C₃₁H₄₀N₄O₈
• 分子量: 596.681
• InChiKey: ZWUPXDWSOWRAAU-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Boc-Pro-Ala-Val 、 (S)-methyl 2-((benzyloxycarbonyl)(methyl)amino)-3-(1-(5-(2-(tertbutoxycarbonylamino)ethyl)-2-(methoxymethoxy)phenyl)-1H-imidazol-4-yl)propanoate 、 三氟乙酸 在 三氟乙酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 生成 benzyl N-[(7S,13S,16S,19S)-27-hydroxy-16-methyl-8,14,17,20-tetraoxo-19-propan-2-yl-2,4,9,15,18,21-hexazatetracyclo[22.3.1.12,5.09,13]nonacosa-1(27),3,5(29),24(28),25-pentaen-7-yl]-N-methylcarbamate;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of Cytochrome c Oxidase

  摘要：

  Arylboronic acid based technology provides a mild, regioselective, and nontoxic N-arylation procedure for accessing the Unusual N-arylated side chain histidine found in the active site of cytochrome c oxidase (CcO) The N-arylated histidine is elaborated to the complete cytochrome c oxidase cyclic pentapeptide cofactor. Molecular modeling of the cofactor provides insight into the dynamic character of the N-aryl bond.

  DOI：

  10.1021/jo901744y
• 作为产物：
  描述：

  5-(2-(tert-butoxycarbonylamino)ethyl)-2-(methoxymethoxy)phenylboronic acid 、 Cbz-MeHis-OMe 在 [Cu(OH)TMEDA]2Cl₂ 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以61%的产率得到(S)-methyl 2-((benzyloxycarbonyl)(methyl)amino)-3-(1-(5-(2-(tertbutoxycarbonylamino)ethyl)-2-(methoxymethoxy)phenyl)-1H-imidazol-4-yl)propanoate
  参考文献：
  名称：

  Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of Cytochrome c Oxidase

  摘要：

  Arylboronic acid based technology provides a mild, regioselective, and nontoxic N-arylation procedure for accessing the Unusual N-arylated side chain histidine found in the active site of cytochrome c oxidase (CcO) The N-arylated histidine is elaborated to the complete cytochrome c oxidase cyclic pentapeptide cofactor. Molecular modeling of the cofactor provides insight into the dynamic character of the N-aryl bond.

  DOI：

  10.1021/jo901744y

文献信息

• Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of Cytochrome <i>c</i> Oxidase
  作者：Maximillian E. Mahoney、Allen Oliver、Ólöf Einarsdóttir、Joseph P. Konopelski

  DOI：10.1021/jo901744y

  日期：2009.11.6

  Arylboronic acid based technology provides a mild, regioselective, and nontoxic N-arylation procedure for accessing the Unusual N-arylated side chain histidine found in the active site of cytochrome c oxidase (CcO) The N-arylated histidine is elaborated to the complete cytochrome c oxidase cyclic pentapeptide cofactor. Molecular modeling of the cofactor provides insight into the dynamic character of the N-aryl bond.