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