benzyl N-[(2S)-1-amino-1-hydroxyimino-3-phenylpropan-2-yl]carbamate | 1058148-74-5

• 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: benzyl N-[(2S)-1-amino-1-hydroxyimino-3-phenylpropan-2-yl]carbamate
• CAS: 1058148-74-5
• 化学式: C₁₇H₁₉N₃O₃
• 分子量: 313.356
• InChiKey: JYQXWXKRAILHMP-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S)-1-amino-1-hydroxyimino-3-phenylpropan-2-yl]carbamate 、 (S)-3-((叔丁氧基羰基)氨基)-4-氟-4-氧代丁酸苄酯 在 N-甲基吗啉 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.25h， 以68%的产率得到benzyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[3-[(1S)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]-1,2,4-oxadiazol-5-yl]propanoate
  参考文献：
  名称：

  Synthesis of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics

  摘要：

  The synthesis of a new class of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics is described. The protocol employs a reaction between an N-protected amino acyl fluoride and an amino acid-derived amidoxime. All the three commonly employed urethanes have been used in this protocol for N-protection. The course of the reaction was found to be high yielding and all new compounds were well characterized by NMR and mass spectroscopy. The C-acyl amidoxime intermediate has also been isolated as a stable solid. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.091
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨腈 在 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 benzyl N-[(2S)-1-amino-1-hydroxyimino-3-phenylpropan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics

  摘要：

  The synthesis of a new class of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics is described. The protocol employs a reaction between an N-protected amino acyl fluoride and an amino acid-derived amidoxime. All the three commonly employed urethanes have been used in this protocol for N-protection. The course of the reaction was found to be high yielding and all new compounds were well characterized by NMR and mass spectroscopy. The C-acyl amidoxime intermediate has also been isolated as a stable solid. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.091