(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 | 1190430-56-8

• 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)-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
• 英文别名: tert-butyl N-[(2S)-1-[[(2S)-1-[[(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]amino]-1,4-dioxo-4-(tritylamino)butan-2-yl]amino]-3-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]carbamate
• CAS: 1190430-56-8
• 化学式: C₇₀H₇₅N₇O₁₁
• 分子量: 1190.41
• InChiKey: FNQOTWGGUVSLAX-FFWKYUIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  88
• 可旋转键数：
  27
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  240
• 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)-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
• 作为产物：
  描述：

  1,1-dimethylethyl (S)-1-{(S)-1,4-dioxo-1-[(S)-1-oxo-1-(2-oxo-3-oxazolidinyl)-3-phenylpropan-2-ylamino]-4-(triphenylmethylamino)butan-2-ylamino}-1,4-dioxo-4-(triphenylmethylamino)butan-2-ylcarbamate 、 N-叔丁氧羰基-O-叔丁基-L-丝氨酸 在 盐酸 、 水 、 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 异丙醇 、 二氯甲烷 为溶剂， 反应 21.0h， 以86%的产率得到(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
  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.