Oseltamivir chemistry

Lew, W., Chen, X. and Kim, C.U. (2000) Discovery and development of GS 4104 (oseltamivir) an orally active influenza neuraminidase inhibitor. Current Medicinal Chemistry, 7, 663-672. 

CHEMISTRY AND ANTIVIRAL ACTIVITY Oseltamivir carboxylate [(3R, 4R, 55)-4-acetylamino-5-amino-3(l-ethylpropoxyl)-l-cyclohexene-l-carboxylic acid] is a sialic acid analog that potently inhibits influenza vims neuraminidases. 

CHEMISTRY AND ANTIVIRAL ACTIVITY Zanamivir (4-guanidino-2,4-dideoxy-2, 3-dehydro-/V-acetyl neuraminic acid) is a siaMc acid analog that potently and specifically inhibits the neuraminidases of influenza A and B viruses. Depending on the strain, zanamivir competitively inhibits influenza neuraminidase activity but affects neuraminidases from other pathogens and mammalian sources only at much higher concentrations. Zanamivir inhibits in vitro replication of influenza A and B viruses, including amantadine- and rimantadine-resistant strains and several oseltamivir-resistant variants. 

From the viewpoint of azide chemistry, the synthesis of Oseltamivir is very interesting in many aspects because azides are used at more than one point and the azide synthesis processes used have prevailed over azide-free alternatives. ... 

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