(S)-methyl 2-[(2S,3S)-2-((S)-2-{(S)-5-[(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}-4-oxo-4-(triphenylmethylamino)butanamido]-4-oxo-6-phenylhexanamido}propanamido)-3-methylpentanamido]-4-methylpentanoate | 1008131-87-0

• 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: (S)-methyl 2-[(2S,3S)-2-((S)-2-{(S)-5-[(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}-4-oxo-4-(triphenylmethylamino)butanamido]-4-oxo-6-phenylhexanamido}propanamido)-3-methylpentanamido]-4-methylpentanoate
• 英文别名: methyl (2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(5S)-5-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-(tritylamino)butanoyl]amino]-4-oxo-6-phenylhexanoyl]amino]propanoyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoate
• CAS: 1008131-87-0
• 化学式: C₆₆H₇₄N₆O₁₀
• 分子量: 1111.35
• InChiKey: CHVFTUQTGQZUBY-QJGCDUQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  82
• 可旋转键数：
  29
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  227
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N-丙烯酰基-L-丙氨酰-L-异亮氨酸-L-亮氨酸甲酯 、 (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 在 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以20%的产率得到(S)-methyl 2-[(2S,3S)-2-((S)-2-{(S)-5-[(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonyl}-4-oxo-4-(triphenylmethylamino)butanamido]-4-oxo-6-phenylhexanamido}propanamido)-3-methylpentanamido]-4-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

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.