4-[(2R,3S)-3-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-azetidin-1-yl]-N-(1-phenyl-1H-pyrazol-3-yl)-benzenesulfonamide | 288585-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[(2R,3S)-3-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-azetidin-1-yl]-N-(1-phenyl-1H-pyrazol-3-yl)-benzenesulfonamide
• CAS: 288585-98-8
• 化学式: C₃₀H₃₀N₄O₆S
• 分子量: 574.657
• InChiKey: AUQZNJURFBMOIF-KZQOYIJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  111.99
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-[(2R,3S)-3-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-azetidin-1-yl]-N-(1-phenyl-1H-pyrazol-3-yl)-benzenesulfonamide 在 对甲苯磺酸 作用下， 以 二甲基亚砜 为溶剂， 以80%的产率得到4-{(2R,3S)-3-(benzyloxy)-2-[(1S)-1,2-dihydroxyethyl]-4-oxoazetidin-1-yl}-N-(1-phenyl-1H-pyrazol-3-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and GC-Eims Analyses of Optically Pure 3-Hydroxy-2-Azetidinones HavingN-Sulfonamide Drugs Side Chain

  摘要：

  A series of new N-sulfonamides of substituted 3-hydroxy-2-azetidinones were prepared by the [2+2] cycloaddition of aldoximes, formed from the condensation of D-(R)-glyceraldehyde acetonide and the potent p-aminophenyl-N-substituted sulfonamides, with benzyloxyacetyl chloride followed by removal of the protecting groups. Obtaining both diastereoisomeric forms of beta-lactams by resorting to kinetic resolution starting from racemic imino analogue is also described. The GC-EIMS, spectroscopic and analytical analyses for some of these derivatives are reported.

  DOI：

  10.1080/00397910008087410
• 作为产物：
  描述：

  sulfaphenazole 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 12.0h， 生成 4-[(2R,3S)-3-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-azetidin-1-yl]-N-(1-phenyl-1H-pyrazol-3-yl)-benzenesulfonamide
  参考文献：
  名称：

  Synthesis and GC-Eims Analyses of Optically Pure 3-Hydroxy-2-Azetidinones HavingN-Sulfonamide Drugs Side Chain

  摘要：

  A series of new N-sulfonamides of substituted 3-hydroxy-2-azetidinones were prepared by the [2+2] cycloaddition of aldoximes, formed from the condensation of D-(R)-glyceraldehyde acetonide and the potent p-aminophenyl-N-substituted sulfonamides, with benzyloxyacetyl chloride followed by removal of the protecting groups. Obtaining both diastereoisomeric forms of beta-lactams by resorting to kinetic resolution starting from racemic imino analogue is also described. The GC-EIMS, spectroscopic and analytical analyses for some of these derivatives are reported.

  DOI：

  10.1080/00397910008087410