Trademarks: Tamiflu
Molecular Formula: C16H28N2O4
CAS Registry Number: 204255-11-8
CAS Name: ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
Molecular Weight: 312.404
SMILES: CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1
InChI Key: VSZGPKBBMSAYNT-RRFJBIMHSA-N
InChI: InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1
Activity: Enzyme Inhibitors; Antiviral Agents; Neuraminidase Inhibitor; Influenza A and B Viruses Treatment; H1N1 flu Treatment; Swine Flu Treatment;
Status: Launched 1999
Originator: Gilead/Roche
Many routes are present in the literature. The most important and notable ones are:
Oseltamivir synthesis: J Am Chem Soc 2006, 128(19), 6310-6311 or Corey's route (Reported by Corey and workers in response to news that Tamiflu supply was short. It is claimed that the scheme was completed in three months. The methodology is not patented, open for more optimization).
References:
1. Corey, E. J.; et. al. A Short Enantioselective Pathway for the Synthesis of the Anti-Influenza Neuramidase Inhibitor Oseltamivir from 1,3-Butadiene and Acrylic Acid. J Am Chem Soc 2006, 128(19), 6310-6311.
2. Trost, B. M.; et. al. A Concise Synthesis of (-)-Oseltamivir. Angew Chem Int Ed 2008, 47(20), 3759-3761.
