4358-72-9Relevant articles and documents
Enantioselective Synthesis of Oseltamivir Phosphate (Tamiflu) via the Iron-Catalyzed Stereoselective Olefin Diazidation
Li, Hongze,Shen, Shou-Jie,Zhu, Cheng-Liang,Xu, Hao
supporting information, p. 10619 - 10626 (2018/08/03)
We herein report a gram-scale, enantioselective synthesis of Tamiflu, in which the key trans-diamino moiety has been efficiently installed via an iron-catalyzed stereoselective olefin diazidation. This significantly improved, iron-catalyzed method is uniquely effective for highly functionalized yet electronically deactivated substrates that have been previously problematic. Preliminary catalyst structure-reactivity-stereoselectivity relationship studies revealed that both the iron catalyst and the complex substrate cooperatively modulate the stereoselectivity for diazidation. Safety assessment using both differential scanning calorimetry (DSC) and the drop weight test (DWT) has also demonstrated the feasibility of carrying out this iron-catalyzed olefin diazidation for large-scale Tamiflu synthesis.
Stereo-specific synthesis of shimikic acid derivatives with improved efficiency
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, (2008/06/13)
The invention provides a multistep synthesis for the preparation of 4,5-diamino shikimic acid derivatives of formula 1starting from an isophthalic acid derivative of formula 24,5-Diamino shikimic acid derivatives are potent inhibitors of viral neuraminidase.