(2,3,4,5,6-pentafluorophenyl) (2R)-2-[(4S)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-3-yl]propanoate | 196795-94-5

• 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: (2,3,4,5,6-pentafluorophenyl) (2R)-2-[(4S)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-3-yl]propanoate
• CAS: 196795-94-5
• 化学式: C₂₀H₁₈F₅NO₃
• 分子量: 415.36
• InChiKey: NRVFMTSCCJIKJR-ZYHUDNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  L-缬氨酸叔丁酯盐酸盐 、 (2,3,4,5,6-pentafluorophenyl) (2R)-2-[(4S)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-3-yl]propanoate 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到tert-butyl (2S)-2-[[(2R)-2-[(4S)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-3-yl]propanoyl]amino]-3-methylbutanoate
  参考文献：
  名称：

  Asymmetric Synthesis of Activated α-Amino Esters via Chromium Carbene Complex Photochemistry

  摘要：

  Optically active chromium aminocarbene complexes were alpha-alkylated and then photolyzed in the presence of 2,4,5-trichlorophenol to produce a number of optically active activated alpha-amino esters. These underwent coupling with amino acid esters or a soluble PEG-supported dipeptide to introduce the chromium-carbene-complex-derived amino acid residue into the peptide.

  DOI：

  10.1021/jo9709817
• 作为产物：
  描述：

  五氟苯酚 、 (4S)-2,2-dimethyl-4-phenyloxazolidine 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (2,3,4,5,6-pentafluorophenyl) (2R)-2-[(4S)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-3-yl]propanoate 、 (S)-2-((S)-2,2-Dimethyl-4-phenyl-oxazolidin-3-yl)-propionic acid pentafluorophenyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of Activated α-Amino Esters via Chromium Carbene Complex Photochemistry

  摘要：

  Optically active chromium aminocarbene complexes were alpha-alkylated and then photolyzed in the presence of 2,4,5-trichlorophenol to produce a number of optically active activated alpha-amino esters. These underwent coupling with amino acid esters or a soluble PEG-supported dipeptide to introduce the chromium-carbene-complex-derived amino acid residue into the peptide.

  DOI：

  10.1021/jo9709817

文献信息

• Asymmetric Synthesis of Activated α-Amino Esters via Chromium Carbene Complex Photochemistry
  作者：Jiawang Zhu、Christopher Deur、Louis S. Hegedus

  DOI：10.1021/jo9709817

  日期：1997.10.1

  Optically active chromium aminocarbene complexes were alpha-alkylated and then photolyzed in the presence of 2,4,5-trichlorophenol to produce a number of optically active activated alpha-amino esters. These underwent coupling with amino acid esters or a soluble PEG-supported dipeptide to introduce the chromium-carbene-complex-derived amino acid residue into the peptide.