(2S,3S)-2-tert-Butoxycarbonylamino-3-(3-methyl-3H-imidazol-4-yl)-butyric acid methyl ester | 897656-12-1

• 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,3S)-2-tert-Butoxycarbonylamino-3-(3-methyl-3H-imidazol-4-yl)-butyric acid methyl ester
• CAS: 897656-12-1
• 化学式: C₁₄H₂₃N₃O₄
• 分子量: 297.354
• InChiKey: IGUXETDZJWDTGQ-KOLCDFICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  82.45
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-tert-Butoxycarbonylamino-3-(3-methyl-3H-imidazol-4-yl)-butyric acid methyl ester 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以88%的产率得到(2S,3S)-3-(3-methylimidazol-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
  参考文献：
  名称：

  Dihedral angle restriction within a peptide-based tertiary alcohol kinetic resolution catalyst

  摘要：

  Kinetic resolution of several tertiary alcohols has been evaluated with a peptide-based catalyst that was designed to probe the role of dihedral angle restrictions for certain bonds within the catalyst. In particular, the nucleophilic residue (pi-Me)-His has been replaced with the (beta-Me)-(pi-Me)-His. A synthesis of the key residue is presented, along with characterization data that suggests the substituent exerts a substantial ground state conformational effect. In addition, kinetic resolution data indicate that the H- to Me-substitution confers enhanced stereoselectivity in several tertiary alcohol resolutions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.104
• 作为产物：
  描述：

  (S)-3-[(2S,3S)-2-Azido-3-(1-benzyl-1H-imidazol-4-yl)-butyryl]-4-phenyl-oxazolidin-2-one 在 palladium on activated charcoal 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -10.0~25.0 ℃ 、101.33 kPa 条件下， 反应 25.0h， 生成 (2S,3S)-2-tert-Butoxycarbonylamino-3-(3-methyl-3H-imidazol-4-yl)-butyric acid methyl ester
  参考文献：
  名称：

  Dihedral angle restriction within a peptide-based tertiary alcohol kinetic resolution catalyst

  摘要：

  Kinetic resolution of several tertiary alcohols has been evaluated with a peptide-based catalyst that was designed to probe the role of dihedral angle restrictions for certain bonds within the catalyst. In particular, the nucleophilic residue (pi-Me)-His has been replaced with the (beta-Me)-(pi-Me)-His. A synthesis of the key residue is presented, along with characterization data that suggests the substituent exerts a substantial ground state conformational effect. In addition, kinetic resolution data indicate that the H- to Me-substitution confers enhanced stereoselectivity in several tertiary alcohol resolutions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.104