5-(dimethylphenylsilyl)pyrrolidine-1,2-dicarboxylic acid 1-benzyl 2-methyl ester | 916049-26-8

• 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: 5-(dimethylphenylsilyl)pyrrolidine-1,2-dicarboxylic acid 1-benzyl 2-methyl ester
• 英文别名: 1-O-benzyl 2-O-methyl (2S)-5-[dimethyl(phenyl)silyl]pyrrolidine-1,2-dicarboxylate
• CAS: 916049-26-8
• 化学式: C₂₂H₂₇NO₄Si
• 分子量: 397.546
• InChiKey: OIHKMQLKSZYDIZ-XJDOXCRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(dimethylphenylsilyl)pyrrolidine-1,2-dicarboxylic acid 1-benzyl 2-methyl ester 在 palladium dihydroxide tetrabutylammonium tetrafluoroborate 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-(2-tert-butoxycarbonylamino-3-hydroxypropionyl)-5-methoxypyrrolidine-2-carboxylic 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：

  1-benzyl 2-methyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate 在 lithium 、 magnesium sulfate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.67h， 生成 5-(dimethylphenylsilyl)pyrrolidine-1,2-dicarboxylic acid 1-benzyl 2-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.