(6S,9S,15S,18S,21S)-phenylmethyl 18-sec-butyl-2,2,15,23-tetramethyl-4,7,10,13,16,19-hexaoxo-6-[2-oxo-2-(triphenylmethylamino)ethyl]-9-phenylmethyl-3-oxa-5,8,14,17,20-pentaazatetracosane-21-carboxylate | 1190430-55-7

• 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,15S,18S,21S)-phenylmethyl 18-sec-butyl-2,2,15,23-tetramethyl-4,7,10,13,16,19-hexaoxo-6-[2-oxo-2-(triphenylmethylamino)ethyl]-9-phenylmethyl-3-oxa-5,8,14,17,20-pentaazatetracosane-21-carboxylate
• 英文别名: benzyl (2S)-4-methyl-2-[[(2S,3S)-3-methyl-2-[[(2S)-2-[[(5S)-5-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-(tritylamino)butanoyl]amino]-4-oxo-6-phenylhexanoyl]amino]propanoyl]amino]pentanoyl]amino]pentanoate
• CAS: 1190430-55-7
• 化学式: C₆₂H₇₆N₆O₁₀
• 分子量: 1065.32
• InChiKey: XCYOSNDAZOYYLS-UFZSZFJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  78
• 可旋转键数：
  30
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  Ala-Ile-Leu-OBn trifluoroacetate 、 (S)-5-[[(S)-2-(tert-butoxycarbonylamino)]-4-oxo-4-(triphenylmethylamino)butanamido]-4-oxo-6-phenylhexanoic acid 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， 以 二氯甲烷 为溶剂， 反应 18.0h， 以80%的产率得到(6S,9S,15S,18S,21S)-phenylmethyl 18-sec-butyl-2,2,15,23-tetramethyl-4,7,10,13,16,19-hexaoxo-6-[2-oxo-2-(triphenylmethylamino)ethyl]-9-phenylmethyl-3-oxa-5,8,14,17,20-pentaazatetracosane-21-carboxylate
  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.