4-{(2R,3S)-3-(benzyloxy)-2-[(1S)-1,2-dihydroxyethyl]-4-oxoazetidin-1-yl}-N-(2,6-dimethoxypyrimidin-4-yl)benzenesulfonamide

• 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: 4-{(2R,3S)-3-(benzyloxy)-2-[(1S)-1,2-dihydroxyethyl]-4-oxoazetidin-1-yl}-N-(2,6-dimethoxypyrimidin-4-yl)benzenesulfonamide
• 英文别名: 4-[(2R,3S)-2-[(1S)-1,2-dihydroxyethyl]-4-oxo-3-phenylmethoxyazetidin-1-yl]-N-(2,6-dimethoxypyrimidin-4-yl)benzenesulfonamide
• 化学式: C₂₄H₂₆N₄O₈S
• 分子量: 530.558
• InChiKey: KPUJEJOSJJSWDV-QIJUGHKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  169
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  磺胺二甲氧嗪 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-[(1S)-1,2-dihydroxyethyl]-4-oxoazetidin-1-yl}-N-(2,6-dimethoxypyrimidin-4-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

文献信息

• Synthesis and GC-Eims Analyses of Optically Pure 3-Hydroxy-2-Azetidinones Having<i>N</i>-Sulfonamide Drugs Side Chain
  作者：Hammed H. A. M. Hassan、Raafat Soliman

  DOI：10.1080/00397910008087410

  日期：2000.7

  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.