1-(2-tert-butoxycarbonylamino-3-hydroxypropionyl)-5-methoxypyrrolidine-2-carboxylic acid methyl ester | 916049-19-9

• 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: 1-(2-tert-butoxycarbonylamino-3-hydroxypropionyl)-5-methoxypyrrolidine-2-carboxylic acid methyl ester
• CAS: 916049-19-9
• 化学式: C₁₅H₂₆N₂O₇
• 分子量: 346.381
• InChiKey: JBHGVMULBCRPAO-QRHSGQBVSA-N

物化性质

• 沸点：
  512.1±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.01
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  114.4
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(2-tert-butoxycarbonylamino-3-hydroxypropionyl)-5-methoxypyrrolidine-2-carboxylic acid methyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以81%的产率得到3-tert-butoxycarbonylamino-4-oxohexahydropyrrolo[2,1-b][1,3]oxazine-6-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：

  BOC-L-丝氨酸 在 N-甲基吗啉 、 tetrabutylammonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 12.42h， 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

文献信息

• Silyl-Substituted Amino Acids:  New Routes to the Construction of Selectively Functionalized Peptidomimetics
  作者：Haizhou Sun、Kevin D. Moeller

  DOI：10.1021/ol025776e

  日期：2002.5.1

  [reaction: see text]. Silylated amino acids have been incorporated into peptides and then converted into N-acyliminium ions with the use of an anodic oxidation reaction. The result is a method for selectively incorporating conformational constraints or external nucleophiles within the peptide.

  [反应：请参见文字]。甲硅烷基化的氨基酸已被掺入肽中，然后利用阳极氧化反应转化为N-酰基亚胺离子。结果是一种在肽内选择性掺入构象限制或外部亲核试剂的方法。