benzyl (2S)-2-[[2-(1-aminocyclobutyl)acetyl]amino]-4-methylpentanoate | 204132-45-6

• 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: benzyl (2S)-2-[[2-(1-aminocyclobutyl)acetyl]amino]-4-methylpentanoate
• CAS: 204132-45-6
• 化学式: C₁₉H₂₈N₂O₃
• 分子量: 332.443
• InChiKey: LLQJBWKLSDNLQU-INIZCTEOSA-N

物化性质

• 沸点：
  490.4±20.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-羧基-N-(2-甲基-2-丙基)-L-缬氨酰氟化物 、 benzyl (2S)-2-[[2-(1-aminocyclobutyl)acetyl]amino]-4-methylpentanoate 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以0.079 g的产率得到benzyl (2S)-4-methyl-2-[[2-[1-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]cyclobutyl]acetyl]amino]pentanoate
  参考文献：
  名称：

  A Concise β-Lactam Route to Short Peptide Segments Containing β,β-Disubstituted β-Amino Acids

  摘要：

  An efficient epimerization-free route toward beta,beta-disubstituted beta-amino acid-containing peptides is described. The methodology involves the use of 4,4-disubstituted-N-Boc beta-lactams as acylating agents, which upon coupling with amino acid esters, promoted by potassium cyanide, give rise to dipeptides with no appreciable racemization. By this procedure short peptide segments containing a four-, five-, or six-membered ring at the beta-position of the beta-amino acid residue have been prepared. The method has also proven to be valuable for the preparation of tripeptides. In addition the sterically hindered amino terminus of the beta-amino acid can undergo peptide couplings under standard conditions.

  DOI：

  10.1021/jo9712862
• 作为产物：
  描述：

  benzyl (2S)-4-methyl-2-[[2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]acetyl]amino]pentanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 benzyl (2S)-2-[[2-(1-aminocyclobutyl)acetyl]amino]-4-methylpentanoate
  参考文献：
  名称：

  A Concise β-Lactam Route to Short Peptide Segments Containing β,β-Disubstituted β-Amino Acids

  摘要：

  An efficient epimerization-free route toward beta,beta-disubstituted beta-amino acid-containing peptides is described. The methodology involves the use of 4,4-disubstituted-N-Boc beta-lactams as acylating agents, which upon coupling with amino acid esters, promoted by potassium cyanide, give rise to dipeptides with no appreciable racemization. By this procedure short peptide segments containing a four-, five-, or six-membered ring at the beta-position of the beta-amino acid residue have been prepared. The method has also proven to be valuable for the preparation of tripeptides. In addition the sterically hindered amino terminus of the beta-amino acid can undergo peptide couplings under standard conditions.

  DOI：

  10.1021/jo9712862