(S)-methyl 5-[[(S)-2-(tert-butoxycarbonylamino)]-4-oxo-4-(triphenylmethylamino)butanamido]-4-oxo-6-phenylhexanoate | 1190430-51-3

• 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: (S)-methyl 5-[[(S)-2-(tert-butoxycarbonylamino)]-4-oxo-4-(triphenylmethylamino)butanamido]-4-oxo-6-phenylhexanoate
• 英文别名: methyl (5S)-5-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-(tritylamino)butanoyl]amino]-4-oxo-6-phenylhexanoate
• CAS: 1190430-51-3
• 化学式: C₄₁H₄₅N₃O₇
• 分子量: 691.824
• InChiKey: YWJYIJKKPHWBPB-HEVIKAOCSA-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：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-methyl 5-[[(S)-2-(tert-butoxycarbonylamino)]-4-oxo-4-(triphenylmethylamino)butanamido]-4-oxo-6-phenylhexanoate 在 三甲基氢氧化锡 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 (S)-5-[[(S)-2-(tert-butoxycarbonylamino)]-4-oxo-4-(triphenylmethylamino)butanamido]-4-oxo-6-phenylhexanoic acid
  参考文献：
  名称：

  Synthesis of a Ketomethylene Isostere of the Fibrillating Peptide SNNFGAILSS

  摘要：

  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.

  DOI：

  10.1021/jo901466b
• 作为产物：
  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 、 丙烯酸甲酯（MA） 在 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 44.5h， 以67%的产率得到(S)-methyl 5-[[(S)-2-(tert-butoxycarbonylamino)]-4-oxo-4-(triphenylmethylamino)butanamido]-4-oxo-6-phenylhexanoate
  参考文献：
  名称：

  Synthesis of a Ketomethylene Isostere of the Fibrillating Peptide SNNFGAILSS

  摘要：

  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.

  DOI：

  10.1021/jo901466b

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.