Stereoisomers of oseltamivir – synthesis, in silico prediction …
2017年1月26日 — We describe herein the stereoselective synthesis, computational activity prediction and biological testing of another three diastereoisomers of oseltamivir. These isomers have been synthesized using stereoselective organocatalytic Michael addition, cyclization and …
Rapid Enantioselective and Diastereoconvergent Hybrid Organic ...
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.
Oseltamivir total synthesis - Wikipedia
The 3,4-pentylidene acetal mesylate is prepared in three steps: esterification with ethanol and thionyl chloride; ketalization with p -toluenesulfonic acid and 3-pentanone; and mesylation with triethylamine and methanesulfonyl chloride.
Two approaches toward the formal total synthesis of oseltamivir ...
2013年4月19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.
Stereoisomers of oseltamivir – synthesis, in silico prediction …
2017年2月3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.
The evolution of Tamiflu synthesis, 20 years on: Advent of …
2020年9月11日 — In the presence of K 2 CO 3 in EtOH, oseltamivir 28 (free base) was afforded [91]. According to Hayashi and coworkers, [91] Tamiflu’s synthesis was accomplished by two ‘one-pot’ reaction sequences, with excellent overall yield (60%) and required only one purification by column chromatography.
Stereoisomers of oseltamivir - synthesis, in silico prediction …
2017年2月22日 — We describe herein the stereoselective synthesis, computational activity prediction and biological testing of another three diastereoisomers of oseltamivir. These isomers have been synthesized using stereoselective organocatalytic Michael addition, cyclization and …
Recent synthetic approaches to oseltamivir phosphate (Tamiflu™) …
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 the rest of chirality at the C4 and C5 positions.
Time Economical Total Synthesis of (−)-Oseltamivir
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.
Two Approaches toward the Formal Total Synthesis of Oseltamivir ...
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.