{2-[2-(dimethylphenylsilyl)-5-(methoxymethyl)pyrrolidin-1-yl]-1-hydroxymethyl-2-oxoethyl}carbamic acid tert-butyl ester | 916049-23-5

• 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-(dimethylphenylsilyl)-5-(methoxymethyl)pyrrolidin-1-yl]-1-hydroxymethyl-2-oxoethyl}carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-[(5S)-2-[dimethyl(phenyl)silyl]-5-(methoxymethyl)pyrrolidin-1-yl]-3-hydroxy-1-oxopropan-2-yl]carbamate
• CAS: 916049-23-5
• 化学式: C₂₂H₃₆N₂O₅Si
• 分子量: 436.624
• InChiKey: GIDBJLOSJVGCER-SPIBDARASA-N

物化性质

• 沸点：
  575.0±50.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {2-[2-(dimethylphenylsilyl)-5-(methoxymethyl)pyrrolidin-1-yl]-1-hydroxymethyl-2-oxoethyl}carbamic acid tert-butyl ester 在 tetrabutylammonium tetrafluoroborate 作用下， 以 异丙醇 、 乙腈 为溶剂， 以80%的产率得到6-methoxymethyl-4-oxohexahydropyrrolo[2,1-b](1,3-oxazin-3-yl)carbamic acid tert-butyl 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：

  L-脯氨醇 在 盐酸 、 氢氧化钾 、 lithium 、 四乙基对甲苯磺酸铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.17h， 生成 {2-[2-(dimethylphenylsilyl)-5-(methoxymethyl)pyrrolidin-1-yl]-1-hydroxymethyl-2-oxoethyl}carbamic acid tert-butyl 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.