(2S)-3-methyl-2-[[2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]acetyl]amino]butanoic acid | 204132-40-1

• 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: (2S)-3-methyl-2-[[2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]acetyl]amino]butanoic acid
• CAS: 204132-40-1
• 化学式: C₁₆H₂₈N₂O₅
• 分子量: 328.409
• InChiKey: HZFWXJRFNMRHSY-LBPRGKRZSA-N

物化性质

• 沸点：
  537.050±33.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.151±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-缬氨酸甲酯 、 (2S)-3-methyl-2-[[2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]acetyl]amino]butanoic acid 在 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以0.296 g的产率得到methyl (2S)-3-methyl-2-[[(2S)-3-methyl-2-[[2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]acetyl]amino]butanoyl]amino]butanoate
  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：

  2-oxo-1-azaspiro[3.3]heptane-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal potassium cyanide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~40.0 ℃ 、101.33 kPa 条件下， 反应 34.0h， 生成 (2S)-3-methyl-2-[[2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]acetyl]amino]butanoic acid
  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