trans-3-<2-(2-tritylaminothiazol-4-yl)-2-((Z)-1-t-butyloxycarbonyl-1-methylethoxyimino)acetamido>-4-ethoxycarbonylmethyl-2-azetidinone | 141992-87-2

• 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-<2-(2-tritylaminothiazol-4-yl)-2-((Z)-1-t-butyloxycarbonyl-1-methylethoxyimino)acetamido>-4-ethoxycarbonylmethyl-2-azetidinone
• CAS: 141992-87-2
• 化学式: C₃₉H₄₃N₅O₇S
• 分子量: 725.866
• InChiKey: PXEKQWZEWKUMCE-SVWCKDAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  52.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  157.31
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  trans-3-<2-(2-tritylaminothiazol-4-yl)-2-((Z)-1-t-butyloxycarbonyl-1-methylethoxyimino)acetamido>-4-ethoxycarbonylmethyl-2-azetidinone 在 吡啶 、 三氟乙酸 作用下， 反应 2.5h， 生成 2-[1-(2-Amino-thiazol-4-yl)-1-((2S,3S)-2-ethoxycarbonylmethyl-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(Z)-ylideneaminooxy]-2-methyl-propionic 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-ethoxycarbonylmethyl-2-azetidinone 在 palladium on activated charcoal 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 trans-3-<2-(2-tritylaminothiazol-4-yl)-2-((Z)-1-t-butyloxycarbonyl-1-methylethoxyimino)acetamido>-4-ethoxycarbonylmethyl-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