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- W2068133035 abstract "Oseltamivir phosphate 1 was synthesized starting from a readily available acetonide, that is, ethyl (3R,4S,5R)-3,4-O-isopropylidene shikimate 2, through a new route via 11 steps and in 44% overall yield. The synthesis described in this article is characterized by two particular steps: the highly regioselective and stereoselective facile nucleophilic replacement of an OMs by an N3 group at the C-3 position of ethyl (3R,4S,5R)-3,4-O-bismethanesulfonyl-5-O-benzoyl shikimate 5, and the mild ring-opening of an aziridine with 3-pentanol at the C-1 position of ethyl (1S,5R,6S)-7-acetyl-5-benzoyloxy-7-azabicyclo[4,1,0]hept-2-ene-3-carboxylate 8." @default.
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- W2068133035 date "2009-01-01" @default.
- W2068133035 modified "2023-09-24" @default.
- W2068133035 title "A novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (−)-shikimic acid" @default.
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- W2068133035 doi "https://doi.org/10.1016/j.tetasy.2008.11.027" @default.
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