N-acetoxy-4-(1-(5-benzyloxycarbonylamino)pentyl)-2-azetidinone | 440353-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: N-acetoxy-4-(1-(5-benzyloxycarbonylamino)pentyl)-2-azetidinone
• 英文别名: [2-Oxo-4-[5-(phenylmethoxycarbonylamino)pentyl]azetidin-1-yl] acetate
• CAS: 440353-71-9
• 化学式: C₁₈H₂₄N₂O₅
• 分子量: 348.399
• InChiKey: IEYDLFMCCUNJNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-acetoxy-4-(1-(5-benzyloxycarbonylamino)pentyl)-2-azetidinone 在 4-二甲氨基吡啶 、 对甲苯磺酰叠氮 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 85.0h， 生成 (+/-)-trans-3-azido-1-(tert-butoxycarbonyl)-4-(1-(5-benzyloxycarbonylamino)pentyl)-2-azetidinone
  参考文献：
  名称：

  An Enantioselective Synthesis of Differentially Protected erythro-α,β-Diamino Acids and Its Application to the Synthesis of an Analogue of Rhodopeptin B5

  摘要：

  Methodology for the enantioselective synthesis of differentially protected erythro-alpha,beta-diamino acids from N-tosyloxy beta-lactams is reported. The requisite N-tosyloxy beta-lactams are readily available from simple beta-keto esters. The reported approach is flexible and compatible with a variety of functional groups. The synthetic utility of the method is demonstrated through its application to the preparation of an analogue of the antifungal cyclic peptide rhodopeptin B5.

  DOI：

  10.1021/jo016276m
• 作为产物：
  描述：

  [[3-Hydroxy-8-(phenylmethoxycarbonylamino)octanoyl]amino] acetate 在 偶氮二甲酸二苄酯 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以73%的产率得到N-acetoxy-4-(1-(5-benzyloxycarbonylamino)pentyl)-2-azetidinone
  参考文献：
  名称：

  An Enantioselective Synthesis of Differentially Protected erythro-α,β-Diamino Acids and Its Application to the Synthesis of an Analogue of Rhodopeptin B5

  摘要：

  Methodology for the enantioselective synthesis of differentially protected erythro-alpha,beta-diamino acids from N-tosyloxy beta-lactams is reported. The requisite N-tosyloxy beta-lactams are readily available from simple beta-keto esters. The reported approach is flexible and compatible with a variety of functional groups. The synthetic utility of the method is demonstrated through its application to the preparation of an analogue of the antifungal cyclic peptide rhodopeptin B5.

  DOI：

  10.1021/jo016276m