trans-3-benzyloxycarbonylamino-4-t-butyloxycarbonylmethylcarbamoylmethyl-2-azetidinone | 142466-77-1

• 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: trans-3-benzyloxycarbonylamino-4-t-butyloxycarbonylmethylcarbamoylmethyl-2-azetidinone
• CAS: 142466-77-1
• 化学式: C₁₉H₂₅N₃O₆
• 分子量: 391.424
• InChiKey: MNQKHNVINGMJDL-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  122.83
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  trans-3-benzyloxycarbonylamino-4-t-butyloxycarbonylmethylcarbamoylmethyl-2-azetidinone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以97%的产率得到[2-((2S,3S)-3-Amino-4-oxo-azetidin-2-yl)-acetylamino]-acetic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and antibacterial activity of C4 substituted monobactams

  摘要：

  The synthesis and antibacterial activity of a series of monobactams having various substituents at C4 position is described. An efficient route to versatile intermediates 4a-c from 6-aminopenicillanic acid (6-APA) has been developed. Derivatives 10e, 11, 21 showed good to moderate activity against Gram-negative bacteria with the exception of Pseudomonas aeruginosa. Introduction of a catechol moiety on the C4 side chain only slightly improved the activity against P aeruginosa.

  DOI：

  10.1016/0223-5234(92)90101-6
• 作为产物：
  描述：

  trans-3-benzyloxycarbonylamino-4-methoxycarbonylmethyl-2-azetidinone 在 potassium carbonate 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 trans-3-benzyloxycarbonylamino-4-t-butyloxycarbonylmethylcarbamoylmethyl-2-azetidinone
  参考文献：
  名称：

  Synthesis and antibacterial activity of C4 substituted monobactams

  摘要：

  The synthesis and antibacterial activity of a series of monobactams having various substituents at C4 position is described. An efficient route to versatile intermediates 4a-c from 6-aminopenicillanic acid (6-APA) has been developed. Derivatives 10e, 11, 21 showed good to moderate activity against Gram-negative bacteria with the exception of Pseudomonas aeruginosa. Introduction of a catechol moiety on the C4 side chain only slightly improved the activity against P aeruginosa.

  DOI：

  10.1016/0223-5234(92)90101-6