[(2R,3S)-2-((R)-3-Isobutoxycarbonyloxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-oxo-acetic acid 4-nitro-benzyl ester | 246848-28-2

• 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: [(2R,3S)-2-((R)-3-Isobutoxycarbonyloxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-oxo-acetic acid 4-nitro-benzyl ester
• 英文别名: (4-nitrophenyl)methyl 2-[(2R,3S)-2-[(2R)-4-(2-methylpropoxycarbonyloxy)-3-oxobutan-2-yl]-4-oxo-3-[(1R)-1-triethylsilyloxyethyl]azetidin-1-yl]-2-oxoacetate
• CAS: 246848-28-2
• 化学式: C₂₉H₄₂N₂O₁₁Si
• 分子量: 622.745
• InChiKey: QOSXOESUKRKNEV-MFVTWZDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  171
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-2-((R)-3-Isobutoxycarbonyloxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-oxo-acetic acid 4-nitro-benzyl ester 在 亚磷酸三乙酯 作用下， 以 正庚烷 为溶剂， 反应 72.0h， 以85%的产率得到[4S-[4α,5β,6β(S*)]]-4-methyl-3-[[[(2-methylpropoxy)carbonyl]oxy]methyl]-7-oxo-6-[1-[(triethylsilyl)oxy]ethyl]-1-azabicyclo[3.2.0]hepten-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester
  参考文献：
  名称：

  Efficient and Practical Synthesis of a Potent Anti-MRSA β-Methylcarbapenem Containing a Releasable Side Chain

  摘要：

  We describe a convergent synthesis of the MRSA beta-methyl carbapenem 1, wherein the molecule is assembled from the naphthosultam side chain 2 and the allylic carbonate of the beta-Me carbapenem piece 6. The beta-Me stereochemistry of 6 is set up in a novel titanium enolate addition into the TBDMS acetoxy azetidinone 5. The benzenesulfonate salt of 1 is endowed with exceptional stability.

  DOI：

  10.1021/ja992486t
• 作为产物：
  描述：

  3-oxobutyl isobutyl carbonate 在 吡啶 、 咪唑 、 盐酸 、 四氯化钛 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 27.0h， 生成 [(2R,3S)-2-((R)-3-Isobutoxycarbonyloxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-oxo-acetic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  Efficient and Practical Synthesis of a Potent Anti-MRSA β-Methylcarbapenem Containing a Releasable Side Chain

  摘要：

  We describe a convergent synthesis of the MRSA beta-methyl carbapenem 1, wherein the molecule is assembled from the naphthosultam side chain 2 and the allylic carbonate of the beta-Me carbapenem piece 6. The beta-Me stereochemistry of 6 is set up in a novel titanium enolate addition into the TBDMS acetoxy azetidinone 5. The benzenesulfonate salt of 1 is endowed with exceptional stability.

  DOI：

  10.1021/ja992486t

文献信息

• Efficient and Practical Synthesis of a Potent Anti-MRSA β-Methylcarbapenem Containing a Releasable Side Chain
  作者：Guy R. Humphrey、Ross A. Miller、Philip J. Pye、Kai Rossen、Robert A. Reamer、Ashok Maliakal、Scott S. Ceglia、Edward J. J. Grabowski、R. P. Volante、Paul J. Reider

  DOI：10.1021/ja992486t

  日期：1999.12.1

  We describe a convergent synthesis of the MRSA beta-methyl carbapenem 1, wherein the molecule is assembled from the naphthosultam side chain 2 and the allylic carbonate of the beta-Me carbapenem piece 6. The beta-Me stereochemistry of 6 is set up in a novel titanium enolate addition into the TBDMS acetoxy azetidinone 5. The benzenesulfonate salt of 1 is endowed with exceptional stability.