101769-63-5Relevant articles and documents
From plant to drug: Ionic liquids for the reactive dissolution of biomass
Ressmann, Anna K.,Gaertner, Peter,Bica, Katharina
, p. 1442 - 1447 (2011)
We present an ionic liquid (IL) strategy for the reactive dissolution of star anise seeds using different Bronsted-acidic ionic liquids as the solvent and reaction media towards the isolation of important pharmaceutical intermediates; this procedure provi
Industrial synthesis of the key precursor in the synthesis of the anti-influenza drug oseltamivir phosphate (Ro 64-0796/002, GS-4104-02): Ethyl (3R,4S,5S)-4,5-epoxy-3-(1-ethyl-propoxy)-cyclohex-1 -ene-1 -carboxylate
Federspiel, Muriel,Fischer, Rolf,Hennig, Michael,Mair, Hans-Jürgen,Oberhauser, Thomas,Rimmler, G?sta,Albiez, Thomas,Bruhin, Jürg,Estermann, Heinrich,Gandert, Carsten,G?ckel, Volker,G?tz?, Stephan,Hoffmann, Ursula,Huber, Gabriel,Janatsch, Günter,Lauper, Stephan,R?ckel-St?bler, Odette,Trussardi, Rene,Zwahlen, Andreas G.
, p. 266 - 274 (1999)
Starting from (-)-quinic acid, the title compound was synthesized in seven chemical steps and an overall yield of 35-38%. The route of the improved Gilead synthesis was not changed. However, significant improvements in each step led to a doubled overall yield, a 30% reduction in the number of unit operations, and an excellent quality (≥99%) of the resulting epoxide. A highly regioselective method for the dehydration of a quinic acid to a shikimic acid derivative and for the reduction of a cyclic ketal was found. Alternatively, the title compound was synthesized in six chemical steps and 63-65% yield from commercially available (-)-shikimic acid. Compared to the optimized quinic acid route, the production time was reduced by about 50%. The quality of epoxide produced from either natural product was equivalent. Therefore (-)-shikimic acid is the preferred raw material. The absolute configuration of the epoxide was determined by X-ray single crystal structure analysis and it was demonstrated that the epoxide was stereo-isomerically pure.
Preparation method for impurity of oseltamivir synthesis process
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Paragraph 0025-0028, (2021/06/26)
The invention provides a preparation method for impurity of an oseltamivir synthesis process. The preparation method comprises the following steps: with shikimic acid as a starting material, successively carrying out an esterification reaction, a Mitsunob
FLOW SYNTHESIS PROCESS FOR THE PRODUCTION OF OSELTAMIVIR
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Page/Page column 7; 12-17, (2020/09/27)
This invention provides for a flow synthesis process for producing Oseltamivir and pharmaceutically acceptable salts thereof from shikimic acid in particular but not exclusively to a flow synthesis process for producing Oseltamivir phosphate from shikimic acid in a nine-step flow synthesis that provides for superior reaction times and product yields compared to known methods.