Stereoisomers of oseltamivir – synthesis, in silico prediction …
网页2017年1月26日 · Oseltamivir is an important antiviral drug, which possess three chirality centers in its structure. From eight possible stereoisomers, only two have been synthesized and evaluated so far. We describe herein the stereoselective synthesis, computational activity prediction and biological testing of another thr.
Oseltamivir total synthesis - Wikipedia
网页Oseltamivir total synthesis concerns the total synthesis of the antiinfluenza drug oseltamivir [1] marketed by Hoffmann-La Roche under the trade name Tamiflu. Its commercial production starts from the biomolecule shikimic acid harvested from Chinese star anise and from recombinant E. coli .
Two Approaches toward the Formal Total Synthesis of Oseltamivir ...
网页2013年3月21日 · Two independent formal total syntheses of oseltamivir phosphate were successfully achieved: the first utilized a copper-catalyzed asymmetric three-component reaction strategy, and the second utilized l-glutamic acid γ-ester as a chiral source to install the correct stereochemistry. Both strategies used Dieckmann condensation to …
The evolution of Tamiflu synthesis, 20 years on: Advent of enabling ...
网页2020年9月9日 · Oseltamivir carboxylate 2 was the first molecule identified by Gilead scientists for development, but the ethyl ester prodrug oseltamivir phosphate (Tamiflu) 1a was ultimately chosen as the clinical candidate based on its potent in vitro and in vivo activities and its good oral bioavailability after extensive diversity-oriented discovery ...
Structural Investigations and Binding Mechanisms of Oseltamivir …
网页2022年7月8日 · The structural and dynamical behaviours of oseltamivir-wildtype and oseltamivir-E119V mutant complexes were investigated through various computational approaches in order to understand the impact of the E119V mutation on resistance to …
Recent synthetic approaches to oseltamivir phosphate (Tamiflu™) …
网页2011年10月14日 · An advantage of this 13-step route to oseltamivir phosphate is the use of very inexpensive ethyl benzoate. The enzymatic oxidation sets the stereochemistry at the C3 position and provides a handle for the introduction of …
Rapid Enantioselective and Diastereoconvergent Hybrid Organic ...
网页2021年4月21日 · A formal synthesis of the antiviral drug (-)-oseltamivir (Tamiflu) has been accomplished starting from m-anisic acid via a dissolving metal or electrochemical Birch reduction. The correct absolute stereochemistry is efficiently set through enzyme-catalyzed carbonyl reduction on the resultant racemic α,β-unsaturated ketone.
Advances on Greener Asymmetric Synthesis of Antiviral Drugs via ...
网页2021年11月4日 · A retro-Michael reaction of the thiol afforded oseltamivir, which was obtained in 82% yield from compound 22 after purification by acid—base extraction. In summary, the efficiency of the Hayashi—Jørgensen organocatalyst was described in the total enantioselective synthesis of (−)-oseltamivir that was carried out in 9 …
Time Economical Total Synthesis of (−)-Oseltamivir
网页2016年7月5日 · A time economical 60 min total synthesis of (−)-oseltamivir was accomplished in a single reaction vessel over five steps. One of the key issues is reduction in the number of steps by eliminating lengthy reaction steps with substitution of a rapid epimerization step.
Stereoisomers of oseltamivir - synthesis, in silico prediction …
网页2017年2月22日 · Oseltamivir is an important antiviral drug, which possess three chirality centers in its structure. From eight possible stereoisomers, only two have been synthesized and evaluated so far. We describe herein the stereoselective synthesis, computational activity prediction and biological testing of an ….