4-nitrobenzyl (4R,5S,6S)-6-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(ethylsulfinyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | 158168-50-4

• 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: 4-nitrobenzyl (4R,5S,6S)-6-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(ethylsulfinyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 158168-50-4
• 化学式: C₂₅H₃₆N₂O₇SSi
• 分子量: 536.722
• InChiKey: STCKWCTXKBGUSB-WSZBTGHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  116.05
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-nitrobenzyl (4R,5S,6S)-6-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(ethylsulfinyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 在 palladium diacetate 甲烷磺酸 、 1,1,2,3-四甲基胍 、 亚磷酸三乙酯 作用下， 反应 3.5h， 生成 (4-nitrophenyl)methyl (4S,5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-3-[[9-(2-hydroxyethyl)-2,2-dioxo-2lambda6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaen-3-yl]methyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Sequential Nitromethane Conjugate Addition/Elimination−Pd-Catalyzed Allylation of β-Trifloxy Acrylates. Application to Carbapenem Synthesis

  摘要：

  [GRAPHICS]Sequential reactions of nitromethane via conjugate addition-elimination to beta-trifloxy acrylates followed by Pd-catalyzed substitution of the resulting allyl nitro compounds with nucleophiles afforded homologation products at the beta-position. 2-Naphthosultammethyl carbapenem, an anti-MRS carbapenem intermediate, was prepared in one pot from the corresponding 2-trifloxy compound. The scope and limitation of the one-pot method were investigated using several cyclic unsaturated esters and nucleophiles.

  DOI：

  10.1021/ol990299u
• 作为产物：
  描述：

  4-Nitrobenzyl (1R,5S,6S)-6-[1(R)-t-butyldimethylsilyloxyethyl]-2-ethylthio-1-methyl-1-carbapen-2-em-3-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到4-nitrobenzyl (4R,5S,6S)-6-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(ethylsulfinyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Sequential Nitromethane Conjugate Addition/Elimination−Pd-Catalyzed Allylation of β-Trifloxy Acrylates. Application to Carbapenem Synthesis

  摘要：

  [GRAPHICS]Sequential reactions of nitromethane via conjugate addition-elimination to beta-trifloxy acrylates followed by Pd-catalyzed substitution of the resulting allyl nitro compounds with nucleophiles afforded homologation products at the beta-position. 2-Naphthosultammethyl carbapenem, an anti-MRS carbapenem intermediate, was prepared in one pot from the corresponding 2-trifloxy compound. The scope and limitation of the one-pot method were investigated using several cyclic unsaturated esters and nucleophiles.

  DOI：

  10.1021/ol990299u