6-(Benzyl-tert-butoxycarbonyl-amino)-hexanoic acid tert-butyl ester | 587840-35-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-(Benzyl-tert-butoxycarbonyl-amino)-hexanoic acid tert-butyl ester
• CAS: 587840-35-5
• 化学式: C₂₂H₃₅NO₄
• 分子量: 377.524
• InChiKey: JUHUIWRKCJZJIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-(Benzyl-tert-butoxycarbonyl-amino)-hexanoic acid tert-butyl ester 在 4-二甲氨基吡啶 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 Tert-butyl 6-[benzyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-2-[1-(4-methylphenyl)sulfonyloxyethyl]hexanoate
  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：

  二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 生成 6-(Benzyl-tert-butoxycarbonyl-amino)-hexanoic 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