N-(tert-butoxycarbonyl)glycyl-[N'-(dimethyl(2,4-dimethoxyphenyl)silyl)methyl]-L-phenylalanine methyl ester | 609347-86-6

• 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: N-(tert-butoxycarbonyl)glycyl-[N'-(dimethyl(2,4-dimethoxyphenyl)silyl)methyl]-L-phenylalanine methyl ester
• 英文别名: 2-((2-tert-butoxycarbonylaminoacetyl){[(2,4-dimethoxyphenyl)dimethylsilanyl]methyl}amino)-3-phenylpropionic acid methyl ester；methyl (2S)-2-[[(2,4-dimethoxyphenyl)-dimethylsilyl]methyl-[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]-3-phenylpropanoate
• CAS: 609347-86-6
• 化学式: C₂₈H₄₀N₂O₇Si
• 分子量: 544.72
• InChiKey: KMLRHHNTOBIOAM-QFIPXVFZSA-N

物化性质

• 沸点：
  661.8±55.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-(tert-butoxycarbonyl)glycyl-[N'-(dimethyl(2,4-dimethoxyphenyl)silyl)methyl]-L-phenylalanine methyl ester 在 ammonium cerium(IV) nitrate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以86%的产率得到N-(tert-butoxycarbonyl)glycyl-[N'-methoxymethyl]-L-phenylalanine methyl ester
  参考文献：
  名称：

  建立功能化的拟肽药物：新型电助剂和使用化学氧化剂将N-酰基亚胺离子引入肽中。

  摘要：

  [反应：见正文]作为将N-酰基亚胺离子插入肽中的方法，已经研究了用化学氧化剂从肽底物上去除电助剂的方法。为此，发现使用硝酸铈铵可容易地裂解4-甲氧基苯基二甲基甲硅烷基和2，4-二甲氧基苯基二甲基甲硅烷基电助剂。在两组中，2,4-二甲氧基苯基二甲基甲硅烷基电助剂在氧化条件下最不稳定。氧化反应被证明与固相底物的使用相容。

  DOI：

  10.1021/ol034872s
• 作为产物：
  描述：

  2,4-二甲氧基溴苯 在 正丁基锂 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 N-(tert-butoxycarbonyl)glycyl-[N'-(dimethyl(2,4-dimethoxyphenyl)silyl)methyl]-L-phenylalanine 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:  New Electroauxiliaries and the Use of a Chemical Oxidant for Introducing <i>N</i>-Acyliminium Ions into Peptides
  作者：Haizhou Sun、Kevin D. Moeller

  DOI：10.1021/ol034872s

  日期：2003.9.1

  [reaction: see text] The removal of electroauxiliaries from peptide substrates with chemical oxidants has been examined as a method for inserting N-acyliminium ions into the peptides. To this end, it was found that both 4-methoxyphenyldimethylsilyl and 2,4-dimethoxyphenyldimethylsilyl electroauxiliaries were readily cleaved with the use of ceric ammonium nitrate. Of the two groups, the 2,4-dimetho

  [反应：见正文]作为将N-酰基亚胺离子插入肽中的方法，已经研究了用化学氧化剂从肽底物上去除电助剂的方法。为此，发现使用硝酸铈铵可容易地裂解4-甲氧基苯基二甲基甲硅烷基和2，4-二甲氧基苯基二甲基甲硅烷基电助剂。在两组中，2,4-二甲氧基苯基二甲基甲硅烷基电助剂在氧化条件下最不稳定。氧化反应被证明与固相底物的使用相容。
• 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.