(3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1R,3R)-3-methoxy-2-oxocyclohexyl]azetidin-2-one | 135413-17-1

• 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: (3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1R,3R)-3-methoxy-2-oxocyclohexyl]azetidin-2-one
• CAS: 135413-17-1
• 化学式: C₁₈H₃₃NO₄Si
• 分子量: 355.55
• InChiKey: OSQWZJJJAOBJJO-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1R,3R)-3-methoxy-2-oxocyclohexyl]azetidin-2-one 在 四丁基氟化铵 、 溶剂黄146 、 三乙胺 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 xylene 为溶剂， 生成 (1S,5R,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-5-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester
  参考文献：
  名称：

  Synthesis and antibacterial activity of 4- and 8-methoxy trinems

  摘要：

  The synthesis of all the isomers of 8-methoxy-(9S,10S,12R)-10-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.2.0.0(3,8])-undec-2-ene-carboxylates 2 and 4-methoxy-(9R,10S,12R)-10-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.2.0.0(3.8)]-undec-2-ene-carboxylates 3 is described. The biological data obtained indicated that the (4S,8S)-4-methoxy derivative (3b) is the best compound in terms of microbiological activity, breadth of spectrum of action and stability to hydrolytic enzymes, namely beta-lactamases.

  DOI：

  10.1016/0960-894x(96)00056-x
• 作为产物：
  描述：

  2-甲氧基环己酮 在 2,6-二甲基吡啶 、 甲酸 、 四丁基氟化铵 、 palladium diacetate 、 potassium hydride 、 sodium hydride 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 18.75h， 生成 (3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1R,3R)-3-methoxy-2-oxocyclohexyl]azetidin-2-one
  参考文献：
  名称：

  A Highly Stereoselective and Practical Total Synthesis of the Tricyclic β-Lactam Antibiotic GV104326 (4-Methoxytrinem)

  摘要：

  A novel and practical total synthesis of a tricyclic beta-lactam antibiotic, GV104326 (4-methoxytrinem or Sanfetrinem) has been achieved in nine steps and about 33% overall yield from a commercially available acetoxyazetidinone chiron. A key step in the highly diastereoselective synthesis is a protonation of a zinc enolate complex which circumvents the use of enantiomerically pure (S)-2-methoxycyclohexanone. A mechanistic rationale is presented and experimentally verified.

  DOI：

  10.1021/ja962006n

文献信息

• The stereoselective synthesis of a key intermediate of the trinem antibiotic sanfetrinem
  作者：Chiara Ghiron、Elisabetta Piga、Tino Rossi、Bruno Tamburini、Russell J. Thomas

  DOI：10.1016/0040-4039(96)00682-x

  日期：1996.5

  By modulating the reactivity of the Lewis acid promoter it was possible to obtain, in a single stereoselective condensation step, the methoxyketone 7, an advanced intermediate in the synthesis of Sanfetrinem GV104326.

  通过调节路易斯酸助催化剂的反应性，可以在单个立体选择性缩合步骤中获得甲氧酮7，这是Sanfetrinem GV104326合成中的高级中间体。
• The use of zinc enolates in the synthesis of a key intermediate for the preparation of trinem antibiotics
  作者：Gordon Kennedy、Tino Rossi、Bruno Tamburini

  DOI：10.1016/0040-4039(96)01606-1

  日期：1996.10

  The stereoselective preparation of 2a, a key intermediate in the synthesis of the broad spectrum tricyclic β-lactam antibiotic GV104326 1, by the reaction of a zinc enolate derived from chiral non-racemic 2-methoxycyclohexanone with azetidinone 3 is described.

  描述了2a的立体选择性制备，这是广谱三环β-内酰胺抗生素GV104326 1合成中的关键中间体，它是通过衍生自手性非外消旋2-甲氧基环己酮的烯醇锌与氮杂环丁酮3反应而制备的。
• A Highly Stereoselective and Practical Total Synthesis of the Tricyclic β-Lactam Antibiotic GV104326 (4-Methoxytrinem)
  作者：Stephen Hanessian、Michael J. Rozema

  DOI：10.1021/ja962006n

  日期：1996.1.1

  A novel and practical total synthesis of a tricyclic beta-lactam antibiotic, GV104326 (4-methoxytrinem or Sanfetrinem) has been achieved in nine steps and about 33% overall yield from a commercially available acetoxyazetidinone chiron. A key step in the highly diastereoselective synthesis is a protonation of a zinc enolate complex which circumvents the use of enantiomerically pure (S)-2-methoxycyclohexanone. A mechanistic rationale is presented and experimentally verified.
• Synthesis and antibacterial activity of 4- and 8-methoxy trinems
  作者：Daniele Andreotti、Tino Rossi、Giovanni Gaviraghi、Daniele Donati、Carla Marchioro、Enza Di Modugno、Alcide Perboni

  DOI：10.1016/0960-894x(96)00056-x

  日期：1996.2

  The synthesis of all the isomers of 8-methoxy-(9S,10S,12R)-10-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.2.0.0(3,8])-undec-2-ene-carboxylates 2 and 4-methoxy-(9R,10S,12R)-10-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.2.0.0(3.8)]-undec-2-ene-carboxylates 3 is described. The biological data obtained indicated that the (4S,8S)-4-methoxy derivative (3b) is the best compound in terms of microbiological activity, breadth of spectrum of action and stability to hydrolytic enzymes, namely beta-lactamases.