p-nitrobenzyl 2-[(3R,4S)-3-(1-(S)-(tert-butyldimethylsilyloxy)propyl)-4-phenylthio-2-azetidinon-1-yl]acetate | 181957-26-6

• 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: p-nitrobenzyl 2-[(3R,4S)-3-(1-(S)-(tert-butyldimethylsilyloxy)propyl)-4-phenylthio-2-azetidinon-1-yl]acetate
• 英文别名: (4-nitrophenyl)methyl 2-[(3R,4S)-3-[(1S)-1-[tert-butyl(dimethyl)silyl]oxypropyl]-2-oxo-4-phenylsulfanylazetidin-1-yl]acetate
• CAS: 181957-26-6
• 化学式: C₂₇H₃₆N₂O₆SSi
• 分子量: 544.744
• InChiKey: ZQUHVBOOYIMTDQ-FBILRYNDSA-N

物化性质

• 沸点：
  643.048±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.210±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-nitrobenzyl 2-[(3R,4S)-3-(1-(S)-(tert-butyldimethylsilyloxy)propyl)-4-phenylthio-2-azetidinon-1-yl]acetate 在 10% palladium on active carbon 吗啉 、 氯化亚砜 、 phosphate buffer 、 四丁基氟化铵 、 氢气 、 溶剂黄146 、 三乙胺 、 二异丙胺 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.75h， 生成 (5R,6R)-6-((S)-1-Hydroxy-propyl)-7-oxo-3-((S)-pyrrolidin-3-ylsulfanyl)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  5,6-cis-Penems:  Broad-Spectrum Anti-Methicillin-Resistant Staphylococcus aureus β-Lactam Antibiotics

  摘要：

  5,6-cis-Penem derivatives have been synthesized and evaluated as anti-MRSA antibiotics. The cis-penems 5 and 6 showed potent activities against not only MRSA but also a wide variety of bacteria including beta-lactamase-producing microorganisms. These compounds were designed to have high affinity to the penicillin-binding protein 2a of MRSA and to form stable acyl intermediates with beta-lactamases by blocking the deacylating water molecule.

  DOI：

  10.1021/jm9703348
• 作为产物：
  描述：

  tert-butyl-dimethyl-[(E,3S)-1-phenylsulfanylpent-1-en-3-yl]oxysilane 在 吡啶 、 potassium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 p-nitrobenzyl 2-[(3R,4S)-3-(1-(S)-(tert-butyldimethylsilyloxy)propyl)-4-phenylthio-2-azetidinon-1-yl]acetate
  参考文献：
  名称：

  5,6-cis-Penems:  Broad-Spectrum Anti-Methicillin-Resistant Staphylococcus aureus β-Lactam Antibiotics

  摘要：

  5,6-cis-Penem derivatives have been synthesized and evaluated as anti-MRSA antibiotics. The cis-penems 5 and 6 showed potent activities against not only MRSA but also a wide variety of bacteria including beta-lactamase-producing microorganisms. These compounds were designed to have high affinity to the penicillin-binding protein 2a of MRSA and to form stable acyl intermediates with beta-lactamases by blocking the deacylating water molecule.

  DOI：

  10.1021/jm9703348

文献信息

• PENEM DERIVATIVES AND ANTIMICROBIAL AGENT CONTAINING THE SAME
  申请人：Daiichi Suntory Pharma Co., Ltd.

  公开号：EP0757051B1

  公开（公告）日：2003-10-29
• 5,6-<i>cis</i>-Penems:  Broad-Spectrum Anti-Methicillin-Resistant <i>Staphylococcus aureus</i> β-Lactam Antibiotics
  作者：Masaji Ishiguro、Rie Tanaka、Koushi Namikawa、Takaaki Nasu、Hidekazu Inoue、Takashi Nakatsuka、Yoshiaki Oyama、Seiichi Imajo

  DOI：10.1021/jm9703348

  日期：1997.7.1

  5,6-cis-Penem derivatives have been synthesized and evaluated as anti-MRSA antibiotics. The cis-penems 5 and 6 showed potent activities against not only MRSA but also a wide variety of bacteria including beta-lactamase-producing microorganisms. These compounds were designed to have high affinity to the penicillin-binding protein 2a of MRSA and to form stable acyl intermediates with beta-lactamases by blocking the deacylating water molecule.