2-({2-[2-((2-benzyloxycarbonylaminoacetyl){[(2,4-dimethoxyphenyl)dimethylsilanyl]methyl}amino)-3-phenylpropionylamino]acetyl}trimethylsilanylmethylamino)-3-phenylpropionic acid methyl ester | 916049-43-9

• 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: 2-({2-[2-((2-benzyloxycarbonylaminoacetyl){[(2,4-dimethoxyphenyl)dimethylsilanyl]methyl}amino)-3-phenylpropionylamino]acetyl}trimethylsilanylmethylamino)-3-phenylpropionic acid methyl ester
• 英文别名: methyl (2S)-2-[[2-[[(2S)-2-[[(2,4-dimethoxyphenyl)-dimethylsilyl]methyl-[2-(phenylmethoxycarbonylamino)acetyl]amino]-3-phenylpropanoyl]amino]acetyl]-(trimethylsilylmethyl)amino]-3-phenylpropanoate
• CAS: 916049-43-9
• 化学式: C₄₆H₆₀N₄O₉Si₂
• 分子量: 869.175
• InChiKey: WZPLXYHHDSQUTG-YDAXCOIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  61
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-({2-[2-((2-benzyloxycarbonylaminoacetyl){[(2,4-dimethoxyphenyl)dimethylsilanyl]methyl}amino)-3-phenylpropionylamino]acetyl}trimethylsilanylmethylamino)-3-phenylpropionic acid methyl ester 、 甲醇 在 ammonium cerium(IV) nitrate 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 以74%的产率得到2-[(2-{2-[(2-benzyloxycarbonylaminoacetyl)methoxymethylamino]-3-phenylpropionylamino}acetyl)trimethylsilanylmethylamino]-3-phenylpropionic acid methyl ester
  参考文献：
  名称：

  Building Functionalized Peptidomimetics:  Use of Electroauxiliaries for Introducing N-Acyliminium Ions into Peptides

  摘要：

  A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.

  DOI：

  10.1021/ja064737l
• 作为产物：
  描述：

  [N-(trimethylsilyl)methyl]-L-phenylalanine methyl ester 在 2,4,6-三甲基吡啶 、 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 2-({2-[2-((2-benzyloxycarbonylaminoacetyl){[(2,4-dimethoxyphenyl)dimethylsilanyl]methyl}amino)-3-phenylpropionylamino]acetyl}trimethylsilanylmethylamino)-3-phenylpropionic acid methyl ester
  参考文献：
  名称：

  Building Functionalized Peptidomimetics:  Use of Electroauxiliaries for Introducing N-Acyliminium Ions into Peptides

  摘要：

  A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.

  DOI：

  10.1021/ja064737l

文献信息

• Building Functionalized Peptidomimetics:  Use of Electroauxiliaries for Introducing <i>N</i>-Acyliminium Ions into Peptides
  作者：Haizhou Sun、Connor Martin、David Kesselring、Rebecca Keller、Kevin D. Moeller

  DOI：10.1021/ja064737l

  日期：2006.10.1

  A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.