9H-fluoren-9-ylmethyl (1S,6E,9aS,9bR)-1-(1-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2-oxo-6-(4-pyridinylmethylidene)-1,2,6,7,8,9,9a,9b-octahydroazeto[2,1-a]isoindole-4-carboxylate | 208191-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl (1S,6E,9aS,9bR)-1-(1-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2-oxo-6-(4-pyridinylmethylidene)-1,2,6,7,8,9,9a,9b-octahydroazeto[2,1-a]isoindole-4-carboxylate
• CAS: 208191-53-1
• 化学式: C₃₉H₄₄N₂O₄Si
• 分子量: 632.875
• InChiKey: UMWZNOGIHLJLFN-ZMZSOGAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  46.0
• 可旋转键数：
  7.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  68.73
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(6R)-2-{(E)-(pyrid-4-yl)methylene}-1-oxocyclohex-6-yl]azetidin-2-one 在 碳酸氢钠 作用下， 以 异辛烷 、 二氯甲烷 、 环己烷 、 水 、 甲苯 为溶剂， 反应 2.5h， 生成 9H-fluoren-9-ylmethyl (1S,6E,9aS,9bR)-1-(1-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2-oxo-6-(4-pyridinylmethylidene)-1,2,6,7,8,9,9a,9b-octahydroazeto[2,1-a]isoindole-4-carboxylate
  参考文献：
  名称：

  The Synthesis of GV143253A: A Case Study for the Use of Analytical and Statistical Tools to Elucidate the Reaction Mechanism and to Optimize the Process

  摘要：

  GV143253A 1 is a broad-spectrum injectable beta-lactam belonging to the class of trinem antibiotics. This article describes the work which enabled a detailed process understanding via several analytical techniques and the subsequent optimization of a key intermediate. By means of a combined application of (31)P NMR spectroscopy and MS spectrometry, the main impurities have been identified and the reaction mechanisms clarified. Moreover, a design of experiments (DoE) approach was applied which substantially improved the overall yield.

  DOI：

  10.1021/op100097c