1,1-dimethylethyl (S)-1,4-dioxo-1-[(S)-1-oxo-1-(2-oxo-3-oxazolidinyl)-3-phenylpropan-2-ylamino]-4-(triphenylmethylamino)butan-2-ylcarbamate | 1008131-74-5

• 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: 1,1-dimethylethyl (S)-1,4-dioxo-1-[(S)-1-oxo-1-(2-oxo-3-oxazolidinyl)-3-phenylpropan-2-ylamino]-4-(triphenylmethylamino)butan-2-ylcarbamate
• 英文别名: tert-butyl N-[(2S)-1,4-dioxo-1-[[(2S)-1-oxo-1-(2-oxo-1,3-oxazolidin-3-yl)-3-phenylpropan-2-yl]amino]-4-(tritylamino)butan-2-yl]carbamate
• CAS: 1008131-74-5
• 化学式: C₄₀H₄₂N₄O₇
• 分子量: 690.796
• InChiKey: BTEMJZASVUZKTG-LQJZCPKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl (S)-1,4-dioxo-1-[(S)-1-oxo-1-(2-oxo-3-oxazolidinyl)-3-phenylpropan-2-ylamino]-4-(triphenylmethylamino)butan-2-ylcarbamate 在 盐酸 作用下， 以 异丙醇 为溶剂， 反应 1.5h， 生成
  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：

  、 叔丁氧羰基-N-beta-三苯甲基-L-天门冬酰胺 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568 mg的产率得到1,1-dimethylethyl (S)-1,4-dioxo-1-[(S)-1-oxo-1-(2-oxo-3-oxazolidinyl)-3-phenylpropan-2-ylamino]-4-(triphenylmethylamino)butan-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

文献信息

• Synthesis of a Ketomethylene Isostere of the Fibrillating Peptide SNNFGAILSS
  作者：Tina Mittag、Daniel E. Otzen、Niels Chr. Nielsen、Troels Skrydstrup

  DOI：10.1021/jo901466b

  日期：2009.10.16

  The direct synthesis of a ketomethylene isostere of the fibril-forming decapeptide SNNFGAILSS is presented with the goal of understanding how small structural changes alter the ability of such peptides to recognize each other for beta-sheet formation. The key synthetic step relies on a SmI2-mediated coupling of a N-tetrapeptidyl oxazolidinone with a simple acrylate followed by deprotection of the carboxylic acid and a peptide coupling step with the pentapeptide H-AILSS-NH2.
• 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.