212504-89-7

Upstream product

• 891831-20-2 (3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene 
• 64-17-5 ethanol 
• 68659-50-7 t-6-Nitro-t-5-acetoxy-3-cyclohexen-r-1-carbonsaeure-aethylester 
• 68659-50-7 (±)-ethyl (1R,5R,6S)-5-acetoxy-6-nitrocyclohex-3-ene-1-carboxylate 
• 949908-55-8 pentan-3-yl 2,2,2-trichloroacetimidate 

Downstream Products

• 1012814-35-5 (3R,4R,5S)-ethyl 4-amino-5-(tert-butoxycarbonylamino)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 
• 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 

Relevant academic research and scientific papers

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.

A method for the synthesis of an oseltamivir PET tracer

A protocol applicable for the synthesis of an oseltamivir positron emission tomography (PET) tracer was developed. Acetylation of amine 3 with CH3COCl, followed by deprotection and aqueous workup, produced oseltamivir 4 from 3 within 10 min. The obtained 4 was sufficiently pure for PET studies. This method can be extended to PET tracer synthesis using CH311COCl.