(2S,3R)-tert-butyl-7-(benzyl-tert-butoxycarbonylamino)-3-(N-benzyl-N-α-(R)-methylbenzylamino)-2-methylheptanoate | 587840-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R)-tert-butyl-7-(benzyl-tert-butoxycarbonylamino)-3-(N-benzyl-N-α-(R)-methylbenzylamino)-2-methylheptanoate
• 英文别名: tert-butyl (2S,3R)-7-[benzyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-[benzyl-[(1R)-1-phenylethyl]amino]-2-methylheptanoate
• CAS: 587840-45-7
• 化学式: C₃₉H₅₄N₂O₄
• 分子量: 614.869
• InChiKey: FKQNFOUSSPESGT-LUFHZVBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-tert-butyl-7-(benzyl-tert-butoxycarbonylamino)-3-(N-benzyl-N-α-(R)-methylbenzylamino)-2-methylheptanoate 在 palladium on activated charcoal 甲酸铵 、 碳酸氢钠 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 生成 (2S,3R)-7-(Benzyl-tert-butoxycarbonyl-amino)-3-benzyloxycarbonylamino-2-methyl-heptanoic acid tert-butyl ester
  参考文献：
  名称：

  Preparation of Protected syn-α,β-Dialkyl β-Amino Acids That Contain Polar Side Chain Functionality

  摘要：

  We report the synthesis of syn-alpha,beta-dialkyl beta-amino acid derivatives suitably protected for solid-phase synthesis that give rise to residues containing positively charged lysine-like side chains. These amino acids, as well as syn-alpha,beta-dialkyl beta-amino acids that contain diverse hydrophobic side chains, are prepared in good de and ee. The key step in this route involves Davies's protocol for the conjugate addition of a chiral lithium amide to alpha,beta-unsaturated tertbutyl esters (Davies, S. G.; Ichihara, O.; Walters, I.A.S.J. Chem. Soc., Perkin Trans. 1 1994, 9, 1141). syn-alpha,beta-Dialkyl beta-amino acids are interesting building blocks because of their sheet-forming propensity and because of their presence in bioactive compounds.

  DOI：

  10.1021/jo034583h
• 作为产物：
  描述：

  benzyl-(5-oxo-pentyl)-carbamic acid tert-butyl acid 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2S,3R)-tert-butyl-7-(benzyl-tert-butoxycarbonylamino)-3-(N-benzyl-N-α-(R)-methylbenzylamino)-2-methylheptanoate
  参考文献：
  名称：

  Preparation of Protected syn-α,β-Dialkyl β-Amino Acids That Contain Polar Side Chain Functionality

  摘要：

  We report the synthesis of syn-alpha,beta-dialkyl beta-amino acid derivatives suitably protected for solid-phase synthesis that give rise to residues containing positively charged lysine-like side chains. These amino acids, as well as syn-alpha,beta-dialkyl beta-amino acids that contain diverse hydrophobic side chains, are prepared in good de and ee. The key step in this route involves Davies's protocol for the conjugate addition of a chiral lithium amide to alpha,beta-unsaturated tertbutyl esters (Davies, S. G.; Ichihara, O.; Walters, I.A.S.J. Chem. Soc., Perkin Trans. 1 1994, 9, 1141). syn-alpha,beta-Dialkyl beta-amino acids are interesting building blocks because of their sheet-forming propensity and because of their presence in bioactive compounds.

  DOI：

  10.1021/jo034583h

文献信息

• Preparation of Protected <i>syn</i>-α,β-Dialkyl β-Amino Acids That Contain Polar Side Chain Functionality
  作者：Joseph M. Langenhan、Samuel H. Gellman

  DOI：10.1021/jo034583h

  日期：2003.8.1

  We report the synthesis of syn-alpha,beta-dialkyl beta-amino acid derivatives suitably protected for solid-phase synthesis that give rise to residues containing positively charged lysine-like side chains. These amino acids, as well as syn-alpha,beta-dialkyl beta-amino acids that contain diverse hydrophobic side chains, are prepared in good de and ee. The key step in this route involves Davies's protocol for the conjugate addition of a chiral lithium amide to alpha,beta-unsaturated tertbutyl esters (Davies, S. G.; Ichihara, O.; Walters, I.A.S.J. Chem. Soc., Perkin Trans. 1 1994, 9, 1141). syn-alpha,beta-Dialkyl beta-amino acids are interesting building blocks because of their sheet-forming propensity and because of their presence in bioactive compounds.