4.1 Article

Facile method for the synthesis of oseltamivir phosphate

Journal

RUSSIAN CHEMICAL BULLETIN
Volume 62, Issue 1, Pages 163-170

Publisher

SPRINGER
DOI: 10.1007/s11172-013-0024-2

Keywords

oseltamivir phosphate; ethyl (3R,4R,5S)-4-acetylamino-5-amino-3-(pent-3-yloxy)cyclohex-1-enecarboxylate; (-)-shikimic acid; aziridines; azides

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A ten-step scheme for the preparation of an antiviral agent, ethyl (3R,4R,5S)-4-acetylamino-5-amino-3-(pent-3-yloxy)cyclohex-1-enecarboxylate phosphate, from (-)-shikimic acid was studied. The main parameters of the synthesis were determined and the optimal conditions for the preparation of the intermediate compounds were selected. The total yield of oseltamivir phosphate calculated based on (-)-shikimic acid was 27%.

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