(5S,6R)-6-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-7-oxo-3-(R)-tetrahydro-furan-2-yl-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester | 181957-23-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5S,6R)-6-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-7-oxo-3-(R)-tetrahydro-furan-2-yl-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (5S,6R)-6-[(1S)-1-[tert-butyl(dimethyl)silyl]oxypropyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 181957-23-3
• 化学式: C₂₂H₃₅NO₅SSi
• 分子量: 453.675
• InChiKey: KMYBPFMVCQQSST-ROYATCLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  90.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5S,6R)-6-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-7-oxo-3-(R)-tetrahydro-furan-2-yl-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 在 四(三苯基膦)钯 、 四丁基氟化铵 、 溶剂黄146 、 三苯基膦 、 sodium 2-ethylhexanoic acid 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 Sodium; (5R,6R)-6-((S)-1-hydroxy-propyl)-7-oxo-3-(R)-tetrahydro-furan-2-yl-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate
  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：

  (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one 在 sodium hydroxide 、 copper diacetate 、 三乙胺 、 亚磷酸三乙酯 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 136.75h， 生成 (5S,6R)-6-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-7-oxo-3-(R)-tetrahydro-furan-2-yl-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
  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.