N-(tert-butoxycarbonyl)-L-valyl-N1-((1S)-1-benzyl-2-{4-[2-[(tert-butoxycarbonyl)amino]-3,3,3-trifluoro-2-(methoxycarbonyl)propyl]-1H-1,2,3-triazol-1-yl}ethyl)-N2-(4-methoxybenzyl)-2-methylalaninamide | 1352924-53-8

• 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: N-(tert-butoxycarbonyl)-L-valyl-N1-((1S)-1-benzyl-2-{4-[2-[(tert-butoxycarbonyl)amino]-3,3,3-trifluoro-2-(methoxycarbonyl)propyl]-1H-1,2,3-triazol-1-yl}ethyl)-N2-(4-methoxybenzyl)-2-methylalaninamide
• 英文别名: methyl 3,3,3-trifluoro-2-[[1-[(2S)-2-[[2-[(4-methoxyphenyl)methyl-[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]-2-methylpropanoyl]amino]-3-phenylpropyl]triazol-4-yl]methyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1352924-53-8
• 化学式: C₄₃H₆₀F₃N₇O₉
• 分子量: 875.986
• InChiKey: IOEHPUKPSGHYDM-MIHTVTFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  62
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  192
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  methyl 2-[(tert-butoxycarbonyl)amino]-2-(trifluoromethyl)pent-4-ynoate 、 N-(tert-butoxycarbonyl)-L-valyl-N1-[(1S)-2-azido-1-benzylethyl]-N2-(4-methoxybenzyl)-2-methylalaninamide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 以85%的产率得到N-(tert-butoxycarbonyl)-L-valyl-N1-((1S)-1-benzyl-2-{4-[2-[(tert-butoxycarbonyl)amino]-3,3,3-trifluoro-2-(methoxycarbonyl)propyl]-1H-1,2,3-triazol-1-yl}ethyl)-N2-(4-methoxybenzyl)-2-methylalaninamide
  参考文献：
  名称：

  Synthesis of CF3-containing tetrapeptide surrogates via Ugi reaction/dipolar cycloaddition sequence

  摘要：

  A convenient synthetic pathway to novel functionalized tetrapeptides containing the 1,2,3-triazole moiety is described. The target molecules were obtained by the reaction of fluorinated alpha-amino acids or alpha-aminophosphonates with azidopeptides via Cu(I)-catalyzed Huisgen cycloaddition reaction (click chemistry). The synthesized tetrapeptides may find important applications in biomedical chemistry as potential drugs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.037

文献信息

• Synthesis of CF3-containing tetrapeptide surrogates via Ugi reaction/dipolar cycloaddition sequence
  作者：Daria V. Vorobyeva、Nadezhda V. Sokolova、Valentine G. Nenajdenko、Alexander S. Peregudov、Sergey N. Osipov

  DOI：10.1016/j.tet.2011.11.037

  日期：2012.1

  A convenient synthetic pathway to novel functionalized tetrapeptides containing the 1,2,3-triazole moiety is described. The target molecules were obtained by the reaction of fluorinated alpha-amino acids or alpha-aminophosphonates with azidopeptides via Cu(I)-catalyzed Huisgen cycloaddition reaction (click chemistry). The synthesized tetrapeptides may find important applications in biomedical chemistry as potential drugs. (C) 2011 Elsevier Ltd. All rights reserved.