Dkpohlkxvwagea-xsektieysa- | 181798-23-2

• 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: Dkpohlkxvwagea-xsektieysa-
• 英文别名: benzyl (1S,5S,8aS,8bR)-1-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-methoxy-2-oxo-5,6,7,8,8a,8b-hexahydro-1H-azeto[1,2-b]isoindole-4-carboxylate
• CAS: 181798-23-2
• 化学式: C₂₇H₃₉NO₅Si
• 分子量: 485.696
• InChiKey: DKPOHLKXVWAGEA-XSEKTIEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Dkpohlkxvwagea-xsektieysa- 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以88%的产率得到Ioehhukouvmzke-qghzaeeisa-
  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 吡啶 、 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 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 xylene 为溶剂， 反应 35.25h， 生成 Dkpohlkxvwagea-xsektieysa-
  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.