methyl (2S,4S)-3-[(2S)-2-[(2-nitrophenyl)sulfonylamino]propanoyl]-2-(trifluoromethyl)-1,3-oxazolidine-4-carboxylate | 1228377-13-6

• 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 (2S,4S)-3-[(2S)-2-[(2-nitrophenyl)sulfonylamino]propanoyl]-2-(trifluoromethyl)-1,3-oxazolidine-4-carboxylate
• CAS: 1228377-13-6
• 化学式: C₁₅H₁₆F₃N₃O₈S
• 分子量: 455.369
• InChiKey: MKEGJMZWIDBTPO-BXGCZWRVSA-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 (2S,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

• 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.