(9H-fluoren-9-yl)methyl 2-((3S,4R)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-oxo-4-((R,E)-2-oxo-3-(pyridin-4-ylmethylene)cyclohexyl)azetidin-1-yl)-2-(diethoxy(methyl)-l5-phosphaneylidene)acetate | 1234051-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-yl)methyl 2-((3S,4R)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-oxo-4-((R,E)-2-oxo-3-(pyridin-4-ylmethylene)cyclohexyl)azetidin-1-yl)-2-(diethoxy(methyl)-l5-phosphaneylidene)acetate
• CAS: 1234051-70-7
• 化学式: C₄₄H₅₇N₂O₇PSi
• 分子量: 785.005
• InChiKey: JLGBSIDQQWTGTP-VYKCAOSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.11
• 重原子数：
  55.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  104.26
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl 2-((3S,4R)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-oxo-4-((R,E)-2-oxo-3-(pyridin-4-ylmethylene)cyclohexyl)azetidin-1-yl)-2-(diethoxy(methyl)-l5-phosphaneylidene)acetate 以 异辛烷 、 二氯甲烷 、 环己烷 、 甲苯 为溶剂， 反应 1.17h， 以7.5 kg的产率得到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
• 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 、 水 、 甲苯 为溶剂， 反应 1.33h， 生成 (9H-fluoren-9-yl)methyl 2-((3S,4R)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-oxo-4-((R,E)-2-oxo-3-(pyridin-4-ylmethylene)cyclohexyl)azetidin-1-yl)-2-(diethoxy(methyl)-l5-phosphaneylidene)acetate
  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