68659-50-7

Upstream product

• 1515-76-0 1-acetoxybuta-1,3-diene 
• 5941-50-4 (E)-ethyl 3-nitroacrylate 
• 68659-55-2 ethyl 2-chloro-3-nitropropanoate 

Downstream Products

• 367252-68-4 (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 204255-11-8 oseltamivir phosphate 
• 212504-89-7 (3R,4R,5S)-ethyl 4,5-diamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 

Relevant academic research and scientific papers

Expedient synthesis of oseltamivir and related compounds via direct olefin diazidation-diamidation reaction

Disclosed herein are improved methods for the preparation of oseltamivir, and intermediates useful thereto.

Enantioselective Synthesis of Oseltamivir Phosphate (Tamiflu) via the Iron-Catalyzed Stereoselective Olefin Diazidation

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.