(2R,5R)-benzyl 2-(but-3-enyl)-5-(7-(tert-butyldimethylsilyloxy)heptyl)pyrrolidine-1-carboxylate | 1260087-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,5R)-benzyl 2-(but-3-enyl)-5-(7-(tert-butyldimethylsilyloxy)heptyl)pyrrolidine-1-carboxylate
• 英文别名: benzyl (2R,5R)-2-but-3-enyl-5-[7-[tert-butyl(dimethyl)silyl]oxyheptyl]pyrrolidine-1-carboxylate
• CAS: 1260087-88-4
• 化学式: C₂₉H₄₉NO₃Si
• 分子量: 487.798
• InChiKey: OYCLZJATXNMQJU-KAYWLYCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.48
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5R)-benzyl 2-(but-3-enyl)-5-(7-(tert-butyldimethylsilyloxy)heptyl)pyrrolidine-1-carboxylate 、 丁烯酮 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以90%的产率得到(2R,5R)-benzyl 2-(7-(tert-butyldimethylsilyloxy)heptyl)-5-((E)-5-oxohex-3-enyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Total synthesis of 275A lehmizidine frog skin alkaloid (or of its enantiomer)

  摘要：

  A concise asymmetric total synthesis of the potentially bioactive 275A lehmizidine frog skin alkaloid (or of its enantiomer) is described. Key features of the protocol include an acyliminium butenyl Grignard addition and a seven-membered intramolecular reductive amination step. Both reactions ensure a high degree of diastereocontrol, with installation of the same relative configuration at the C3, C5 and C10 stereocentres as in the natural product 275A. Despite this total synthesis, the absolute configuration of the natural product remains unknown, due to the lack of specific rotation data for alkaloid 275A. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.08.014
• 作为产物：
  描述：

  (2R,5S)-benzyl 2-(but-3-enyl)-5-(tosyloxymethyl)pyrrolidine-1-carboxylate 、 (6-溴己氧基)-叔丁基二甲基硅烷 在 copper(l) iodide 作用下， 反应 24.0h， 生成 (2R,5R)-benzyl 2-(but-3-enyl)-5-(7-(tert-butyldimethylsilyloxy)heptyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Total synthesis of 275A lehmizidine frog skin alkaloid (or of its enantiomer)

  摘要：

  A concise asymmetric total synthesis of the potentially bioactive 275A lehmizidine frog skin alkaloid (or of its enantiomer) is described. Key features of the protocol include an acyliminium butenyl Grignard addition and a seven-membered intramolecular reductive amination step. Both reactions ensure a high degree of diastereocontrol, with installation of the same relative configuration at the C3, C5 and C10 stereocentres as in the natural product 275A. Despite this total synthesis, the absolute configuration of the natural product remains unknown, due to the lack of specific rotation data for alkaloid 275A. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.08.014