(3S,4R)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-(3-methoxy-2-oxocyclohexyl)azetidin-2-one | 188396-12-5

• 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)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-(3-methoxy-2-oxocyclohexyl)azetidin-2-one
• CAS: 188396-12-5
• 化学式: C₂₄H₄₇NO₄Si₂
• 分子量: 469.812
• InChiKey: UYJGQVVILHJYGX-AWUBQHKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-(3-methoxy-2-oxocyclohexyl)azetidin-2-one 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以63%的产率得到(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
• 作为产物：
  描述：

  2-甲氧基环己酮 在 2,6-二甲基吡啶 、 甲酸 、 palladium diacetate 、 potassium hydride 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 17.75h， 生成 (3S,4R)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-(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

• 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.