(3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one | 181957-20-0

• 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: (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one
• 英文别名: (3R,4S)-3-[(1S)-1-[tert-butyl(dimethyl)silyl]oxypropyl]-4-phenylsulfanylazetidin-2-one
• CAS: 181957-20-0
• 化学式: C₁₈H₂₉NO₂SSi
• 分子量: 351.585
• InChiKey: YOWQVLWCXQGDHS-UXLLHSPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one 在 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 p-nitrobenzyl 2-[bis(benzoylthio)methylidene]-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
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 tert-butyl-dimethyl-[(E,3S)-1-phenylsulfanylpent-1-en-3-yl]oxysilane 在 吡啶 、 苯硫酚 作用下， 生成 (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one 、 (3S,4R)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one
  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

• 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.