benzyl (2S)-2-[[2-chloro-2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]acetyl]amino]-4-methylpentanoate | 204132-43-4

• 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-chloro-2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]acetyl]amino]-4-methylpentanoate
• CAS: 204132-43-4
• 化学式: C₂₄H₃₅ClN₂O₅
• 分子量: 467.005
• InChiKey: NRGRALKLEGPKKI-OYKVQYDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (2S)-2-[[2-chloro-2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]acetyl]amino]-4-methylpentanoate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以51%的产率得到(2S)-4-methyl-2-[[2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]acetyl]amino]pentanoic 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
• 作为产物：
  描述：

  2-Oxo-1-aza-spiro[3.3]heptane-1-sulfonyl chloride 在 4-二甲氨基吡啶 、 potassium cyanide 、 氢氧化钾 、 对甲苯磺酰氯 、 sodium sulfite 、 lithium diisopropyl amide 作用下， 以 乙醚 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 17.5h， 生成 benzyl (2S)-2-[[2-chloro-2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]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