butyl (S)-5-[(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}-4-oxo-4-(triphenylmethylamino)butanamido]-4-oxo-6-phenylhexanoate | 1008131-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: butyl (S)-5-[(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}-4-oxo-4-(triphenylmethylamino)butanamido]-4-oxo-6-phenylhexanoate
• 英文别名: butyl (5S)-5-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-(tritylamino)butanoyl]amino]-4-oxo-6-phenylhexanoate
• CAS: 1008131-66-5
• 化学式: C₅₄H₅₃N₃O₇
• 分子量: 856.031
• InChiKey: DAPYUBREXUDWND-CRKOEVGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  64
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (9H-fluoren-9-yl)methyl (S)-1,4-dioxo-1-[(S)-1-oxo-1-(2-oxo-3-oxazolidinyl)-3-phenylpropan-2-ylamino]-4-(triphenylmethylamino)butan-2-ylcarbamate 、 丙烯酸丁酯 在 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以55%的产率得到butyl (S)-5-[(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}-4-oxo-4-(triphenylmethylamino)butanamido]-4-oxo-6-phenylhexanoate
  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

文献信息

• Direct Entry to Peptidyl Ketones via SmI₂-Mediated C−C Bond Formation with Readily Accessible <i>N</i>-Peptidyl Oxazolidinones
  作者：Tina Mittag、Kasper L. Christensen、Karl B. Lindsay、Niels Christian Nielsen、Troels Skrydstrup

  DOI：10.1021/jo702286b

  日期：2008.2.1

  [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.