methyl (2R,4S)-3-[(2S)-2-[(2-nitrophenyl)sulfonylamino]propanoyl]-2-(trifluoromethyl)-1,3-oxazolidine-4-carboxylate | 1228377-14-7

• 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: methyl (2R,4S)-3-[(2S)-2-[(2-nitrophenyl)sulfonylamino]propanoyl]-2-(trifluoromethyl)-1,3-oxazolidine-4-carboxylate
• CAS: 1228377-14-7
• 化学式: C₁₅H₁₆F₃N₃O₈S
• 分子量: 455.369
• InChiKey: MKEGJMZWIDBTPO-QEVYDEPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (2S)-2-[(2-nitrobenzene)sulfonamido]propanoic acid 在 2,3,5-三甲基吡啶 、 1-氯-N,N,2-三甲基丙烯胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl (2R,4S)-3-[(2S)-2-[(2-nitrophenyl)sulfonylamino]propanoyl]-2-(trifluoromethyl)-1,3-oxazolidine-4-carboxylate 、
  参考文献：
  名称：

  Incorporation of CF₃–Pseudoprolines into Peptides: A Methodological Study

  摘要：

  The peptide coupling reactions allowing the incorporation of trifluoromethyl substituted oxazolidine-type pseudoprolines (CF3-Psi Pro) into peptide chains have been studied. While standard protocols can be used for the peptide coupling reaction at the C-terminal position of the CF3-Psi Pro, acid chloride activation has to be used for the peptide coupling reaction at the N-terminal position to overcome the decrease of nucleophilicity of the CF3-Psi Pro. We demonstrate that the N-amidification of a diastereomeric mixture of CF3-Psi Pro using Fmoc-protected amino acid chloride without base gave the corresponding dipeptides as a single diastereomer (6 examples). The ratio of the cis and trans amide bond conformers was determined by NMR study, highlighting the role of the Xaa side chains in the control of the peptide backbone conformation. Finally a tripeptide bearing a central CF3-Psi Pro has been successfully synthesized.

  DOI：

  10.1021/jo401494q

文献信息

• Conformational properties of peptides incorporating a fluorinated pseudoproline residue
  作者：Grégory Chaume、Debby Feytens、Gérard Chassaing、Solange Lavielle、Thierry Brigaud、Emeric Miclet

  DOI：10.1039/c3nj41084f

  日期：——

  We have recently reported the synthesis of enantiomerically pure CF3-oxazolidine pseudoprolines (CF3-ΨPro). Complete NMR studies, together with DFT calculations, have highlighted the marked stereoelectronic effects of the CF3 group on these new proline surrogates. In this paper, we describe for the first time the conformational features of dipeptides incorporating one CF3-ΨPro residue. Extensive NMR analyses have been carried out in solution and revealed the presence of a stable type-VI β-turn in a pseudotetrapeptide sequence.

  我们最近报道了对映体纯的 CF3-恶唑烷假脯氨酸 (CF3-ΨPro) 的合成。完整的 NMR 研究以及 DFT 计算强调了 CF3 基团对这些新脯氨酸替代物的显着立体电子效应。在本文中，我们首次描述了包含一个 CF3-ΨPro 残基的二肽的构象特征。在溶液中进行了广泛的 NMR 分析，并揭示了假四肽序列中存在稳定的 VI 型 β-转角。
• Synthesis of 2-Trifluoromethyl-1,3-oxazolidines as Hydrolytically Stable Pseudoprolines
  作者：Grégory Chaume、Olivier Barbeau、Philippe Lesot、Thierry Brigaud

  DOI：10.1021/jo100518t

  日期：2010.6.18

  Trifluoromethyl group containing oxazolidines (Fox) are conveniently synthesized by condensation of serine esters with trifluoroacetaldehyde hemiacetal or trifluoroacetone. These oxazolidines can undergo N-acylation and amidification reactions and are completely configurationally and hydrolytically stable. Therefore, they can be considered as highly valuable proline surrogates (Tfm-pseudoprolines).
• Incorporation of CF₃–Pseudoprolines into Peptides: A Methodological Study
  作者：Grégory Chaume、Julien Simon、Caroline Caupène、Nathalie Lensen、Emeric Miclet、Thierry Brigaud

  DOI：10.1021/jo401494q

  日期：2013.10.18

  The peptide coupling reactions allowing the incorporation of trifluoromethyl substituted oxazolidine-type pseudoprolines (CF3-Psi Pro) into peptide chains have been studied. While standard protocols can be used for the peptide coupling reaction at the C-terminal position of the CF3-Psi Pro, acid chloride activation has to be used for the peptide coupling reaction at the N-terminal position to overcome the decrease of nucleophilicity of the CF3-Psi Pro. We demonstrate that the N-amidification of a diastereomeric mixture of CF3-Psi Pro using Fmoc-protected amino acid chloride without base gave the corresponding dipeptides as a single diastereomer (6 examples). The ratio of the cis and trans amide bond conformers was determined by NMR study, highlighting the role of the Xaa side chains in the control of the peptide backbone conformation. Finally a tripeptide bearing a central CF3-Psi Pro has been successfully synthesized.