benzhydryl (2S,2'S,5R,6R)-2'-[tert-butyl(dimethyl)silyl]oxy-3,3-dimethyl-4,4,7-trioxospiro[4lambda6-thia-1-azabicyclo[3.2.0]heptane-6,1'-cyclopropane]-2-carboxylate | 562068-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzhydryl (2S,2'S,5R,6R)-2'-[tert-butyl(dimethyl)silyl]oxy-3,3-dimethyl-4,4,7-trioxospiro[4lambda6-thia-1-azabicyclo[3.2.0]heptane-6,1'-cyclopropane]-2-carboxylate
• 英文别名: benzhydryl (2S,2'S,5R,6R)-2'-[tert-butyl(dimethyl)silyl]oxy-3,3-dimethyl-4,4,7-trioxospiro[4λ6-thia-1-azabicyclo[3.2.0]heptane-6,1'-cyclopropane]-2-carboxylate
• CAS: 562068-31-9
• 化学式: C₂₉H₃₇NO₆SSi
• 分子量: 555.767
• InChiKey: UIEWZRADLWFAFK-TXXFMCBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzhydryl (2S,2'S,5R,6R)-2'-[tert-butyl(dimethyl)silyl]oxy-3,3-dimethyl-4,4,7-trioxospiro[4lambda6-thia-1-azabicyclo[3.2.0]heptane-6,1'-cyclopropane]-2-carboxylate 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 以54%的产率得到
  参考文献：
  名称：

  Spirocyclopropyl β-Lactams as Mechanism-Based Inhibitors of Serine β-Lactamases. Synthesis by Rhodium-Catalyzed Cyclopropanation of 6-Diazopenicillanate Sulfone

  摘要：

  Class A-class C mechanism-based beta-lactamase inhibitors were designed on the basis of the intermediacy of an oxycarbenium species capable of cross-linking with amino acids residues in the active site. Penams 24 and 27 were very potent against AmpC in vitro. The MIC values of 24 in combination with piperacillin against class A and class C producing organisms showed improvement over clinically used tazobactam.

  DOI：

  10.1021/jm034056q
• 作为产物：
  描述：

  6-氨基青霉烷酸 在 dirhodium tetraacetate 、 potassium permanganate 、 高氯酸 、 硫酸 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 生成 benzhydryl (2S,2'S,5R,6R)-2'-[tert-butyl(dimethyl)silyl]oxy-3,3-dimethyl-4,4,7-trioxospiro[4lambda6-thia-1-azabicyclo[3.2.0]heptane-6,1'-cyclopropane]-2-carboxylate
  参考文献：
  名称：

  Spirocyclopropyl β-Lactams as Mechanism-Based Inhibitors of Serine β-Lactamases. Synthesis by Rhodium-Catalyzed Cyclopropanation of 6-Diazopenicillanate Sulfone

  摘要：

  Class A-class C mechanism-based beta-lactamase inhibitors were designed on the basis of the intermediacy of an oxycarbenium species capable of cross-linking with amino acids residues in the active site. Penams 24 and 27 were very potent against AmpC in vitro. The MIC values of 24 in combination with piperacillin against class A and class C producing organisms showed improvement over clinically used tazobactam.

  DOI：

  10.1021/jm034056q

文献信息

• Spirocyclopropyl β-Lactams as Mechanism-Based Inhibitors of Serine β-Lactamases. Synthesis by Rhodium-Catalyzed Cyclopropanation of 6-Diazopenicillanate Sulfone
  作者：Vincent P. Sandanayaka、Amar S. Prashad、Youjun Yang、R. Thomas Williamson、Yang I. Lin、Tarek S. Mansour

  DOI：10.1021/jm034056q

  日期：2003.6.1

  Class A-class C mechanism-based beta-lactamase inhibitors were designed on the basis of the intermediacy of an oxycarbenium species capable of cross-linking with amino acids residues in the active site. Penams 24 and 27 were very potent against AmpC in vitro. The MIC values of 24 in combination with piperacillin against class A and class C producing organisms showed improvement over clinically used tazobactam.