(-)-tert-butyl (2R,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate | 222847-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (-)-tert-butyl (2R,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate
• CAS: 222847-41-8
• 化学式: C₃₀H₄₅NO₅Si₂
• 分子量: 555.862
• InChiKey: ISDAWQGMFHFJIP-FTJBHMTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (-)-tert-butyl (2R,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate 在 potassium hydrogen bifluoride 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以94%的产率得到(-)-tert-butyl (2R,3S)-2-[(tert-butyldimethylsiloxy)methyl]-4-hydroxy-5-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  Fleming−Tamao Oxidation and Masked Hydroxyl Functionality:  Total Synthesis of (+)-Pramanicin and Structural Elucidation of the Antifungal Natural Product (−)-Pramanicin

  摘要：

  The total synthesis of (+)-pramanicin (41b) is reported, thereby establishing the relative and absolute stereochemistry of the naturally occurring antifungal agent. The key steps involve (i) conjugate addition of the diethyl((diethylamino)diphenylsilyl)zincate to a suitably protected gamma-lactam 3 and quenching of the resultant enolate with the alpha,beta-unsaturated gamma,delta-epoxy aldehyde 2 (X = H), (ii) Ni(acac)(2)-catalyzed hydroxylation of a beta-dicarbonyl array, and (iii) Fleming-Tamao oxidation to reveal the masked C-3 hydroxyl group.

  DOI：

  10.1021/jo9905672
• 作为产物：
  描述：

  (2S,3R)-N-(叔-丁基氧羰基)-O-(叔-丁基)二甲基硅烷基-3,4-去氢-焦谷氨醇 在 diethylzinc 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (-)-tert-butyl (2R,3S)-2-[(tert-butyldimethylsiloxy)methyl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  Fleming−Tamao Oxidation and Masked Hydroxyl Functionality:  Total Synthesis of (+)-Pramanicin and Structural Elucidation of the Antifungal Natural Product (−)-Pramanicin

  摘要：

  The total synthesis of (+)-pramanicin (41b) is reported, thereby establishing the relative and absolute stereochemistry of the naturally occurring antifungal agent. The key steps involve (i) conjugate addition of the diethyl((diethylamino)diphenylsilyl)zincate to a suitably protected gamma-lactam 3 and quenching of the resultant enolate with the alpha,beta-unsaturated gamma,delta-epoxy aldehyde 2 (X = H), (ii) Ni(acac)(2)-catalyzed hydroxylation of a beta-dicarbonyl array, and (iii) Fleming-Tamao oxidation to reveal the masked C-3 hydroxyl group.

  DOI：

  10.1021/jo9905672