N-acryloyl-L-alanyl-L-isoleucine methyl ester | 1008131-93-8

• 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-acryloyl-L-alanyl-L-isoleucine methyl ester
• CAS: 1008131-93-8
• 化学式: C₁₃H₂₂N₂O₄
• 分子量: 270.329
• InChiKey: BXBINVNUBPSDTB-QXEWZRGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  84.5
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-acryloyl-L-alanyl-L-isoleucine methyl ester 、 1,1-dimethylethyl (2S,3S)-3-methyl-1-{(S)-1-[(S)-4-methyl-1-oxo-1-(2-oxo-3-oxazolidinyl)pentan-2-ylamino]-1-oxo-3-phenylpropan-2-ylamino}-1-oxopentan-2-ylcarbamate 在 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以38%的产率得到(2S,3S)-methyl 2-[(S)-2-((S)-5-{(S)-2-[(2S,3S)-2-(1,1-dimethylethoxycarbonyl)-3-methylpentanamido]-3-phenylpropanamido}-7-methyl-4-oxooctanamido)propanamido]-3-methylpentanoate
  参考文献：
  名称：

  Direct Entry to Peptidyl Ketones via SmI₂-Mediated C−C Bond Formation with Readily Accessible N-Peptidyl Oxazolidinones

  摘要：

  [GRAPHICS]In this work, a new method for the preparation of peptidyl ketones is presented employing a SmI2/H2O-mediated coupling of N-peptidyl oxazolidinones with electron-deficient alkenes. The requisite peptide imides were easily prepared by solution-phase peptide synthesis starting from an N-acyl oxazolidinone derivative of an amino acid. Importantly, they could be used directly in the C-C bond-forming step without the need for further functionalization. Coupling of these peptide derivatives with a second peptide possessing an N-terminal acryloyl group leads to ketomethylene isosteres of glycine-containing peptides. This method represents an alternative means for ligating two small peptides through a C-C bond-forming step.

  DOI：

  10.1021/jo702286b