1,1-dimethylethyl (S)-4-methyl-1-((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-ylamino)-1-oxopentan-2-ylcarbamate | 1008131-73-4

• 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: 1,1-dimethylethyl (S)-4-methyl-1-((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-ylamino)-1-oxopentan-2-ylcarbamate
• CAS: 1008131-73-4
• 化学式: C₃₅H₅₅N₅O₈
• 分子量: 673.85
• InChiKey: NOSOIUMIVICJBP-BLVAWXTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  48.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  172.24
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl (S)-4-methyl-1-((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-ylamino)-1-oxopentan-2-ylcarbamate 、 N-叔丁基丙烯酰胺 在 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以45%的产率得到1,1-dimethylethyl (S)-1-((2S,3S)-1-{(S)-1-[(S)-8-(1,1-dimethylethan-1-ylamino)-2-methyl-5,8-dioxooctan-4-ylamino]-1-oxo-3-phenylpropan-2-ylamino}-3-methyl-1-oxopentan-2-ylamino)-4-methyl-1-oxopentan-2-ylcarbamate
  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
• 作为产物：
  描述：

  、 BOC-L-亮氨酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 反应 48.0h， 以145 mg的产率得到1,1-dimethylethyl (S)-4-methyl-1-((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-ylamino)-1-oxopentan-2-ylcarbamate
  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