(S)-3-[(2S,3S)-2-Azido-3-(1-benzyl-1H-imidazol-4-yl)-butyryl]-4-phenyl-oxazolidin-2-one | 409102-40-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-[(2S,3S)-2-Azido-3-(1-benzyl-1H-imidazol-4-yl)-butyryl]-4-phenyl-oxazolidin-2-one
• CAS: 409102-40-5
• 化学式: C₂₃H₂₂N₆O₃
• 分子量: 430.466
• InChiKey: ZVILVPDUWCJZHM-HBGVWJBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  113.19
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  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， 反应 1.0h， 生成
  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-[(S)-3-(1-Benzyl-1H-imidazol-4-yl)-butyryl]-4-phenyl-oxazolidin-2-one 在 双(三甲基硅烷基)氨基钾 、 2,4,6-三异丙基苯磺酰叠氮化物 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到(S)-3-[(2S,3S)-2-Azido-3-(1-benzyl-1H-imidazol-4-yl)-butyryl]-4-phenyl-oxazolidin-2-one
  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

文献信息

• Asymmetric Azidation−Cycloaddition with Open-Chain Peptide-Based Catalysts. A Sequential Enantioselective Route to Triazoles
  作者：David J. Guerin、Scott J. Miller

  DOI：10.1021/ja0177814

  日期：2002.3.1

  A family of beta-substituted histidine-containing peptides has been synthesized to probe the effect of noncovalent conformational rigidification on catalyst enantioselectivity. Unambiguous enhancement of enantioselectivity in the conjugate addition of azide to alpha,beta-unsaturated carboxylate derivatives has been achieved, enabling application to a sequential asymmetric azidation/cycloaddition for the synthesis of optically enriched triazoles and triazolines.