(6S,9S,12S,15S)-phenylmethyl 6-(tert-butoxymethyl)-2,2-dimethyl-4,7,10,13,16-pentaoxo-9,12-di-[2-oxo-2-(triphenylmethylamino)ethyl]-15-phenylmethyl-3-oxa-5,8,11,14-tetraazanonadecan-19-oate | 1190430-57-9

• 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: (6S,9S,12S,15S)-phenylmethyl 6-(tert-butoxymethyl)-2,2-dimethyl-4,7,10,13,16-pentaoxo-9,12-di-[2-oxo-2-(triphenylmethylamino)ethyl]-15-phenylmethyl-3-oxa-5,8,11,14-tetraazanonadecan-19-oate
• 英文别名: benzyl (5S)-5-[[(2S)-2-[[(2S)-2-[[(2S)-3-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-4-oxo-4-(tritylamino)butanoyl]amino]-4-oxo-4-(tritylamino)butanoyl]amino]-4-oxo-6-phenylhexanoate
• CAS: 1190430-57-9
• 化学式: C₇₇H₈₂N₆O₁₁
• 分子量: 1267.53
• InChiKey: LPFXNAZBEKJKPG-YKIMTJKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  94
• 可旋转键数：
  33
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  236
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (6S,9S,12S,15S)-phenylmethyl 6-(tert-butoxymethyl)-2,2-dimethyl-4,7,10,13,16-pentaoxo-9,12-di-[2-oxo-2-(triphenylmethylamino)ethyl]-15-phenylmethyl-3-oxa-5,8,11,14-tetraazanonadecan-19-oate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 22.0h， 以79%的产率得到(6S,9S,12S,15S)-6-(tert-butoxymethyl)-2,2-dimethyl-4,7,10,13,16-pentaoxo-9,12-di-[2-oxo-2-(triphenylmethylamino)ethyl]-15-phenylmethyl-3-oxa-5,8,11,14-tetraazanonadecan-19-oic 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：

  (6S,9S,12S,15S)-6-(tert-butoxymethyl)-2,2-dimethyl-4,7,10,13,16-pentaoxo-16-(2-oxooxazolidin-3-yl)-9,12-di-[2-oxo-2-(triphenylmethylamino)ethyl]-15-phenylmethyl-3-oxa-5,8,11,14-tetraaza-hexadecane 、 丙烯酸苄酯 在 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 18.17h， 以72%的产率得到(6S,9S,12S,15S)-phenylmethyl 6-(tert-butoxymethyl)-2,2-dimethyl-4,7,10,13,16-pentaoxo-9,12-di-[2-oxo-2-(triphenylmethylamino)ethyl]-15-phenylmethyl-3-oxa-5,8,11,14-tetraazanonadecan-19-oate
  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.