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- W1543282883 abstract "tert-Butyl (±)-7-amino-3-trifluoromethyl-3-cephem-4-carboxylate (16) and the 2-cephem derivative (21) were obtained by total synthesis starting from tert-butyl N-benzylideneglycinate (1). This synthesis is the first example of the reaction of the N-benzylideneglycinate anion with a reactive α-haloketone to give a β-hydroxy-γ-halo-α-aminoester (5a and 5b). The amino esters were treated with ethyl thioformate and then potassium carbonate, leading to the 4, 5-dihydro-6H-1, 3-thiazine derivatives (8a and 8b). After cycloaddition of 8a and 8b with azidoacetyl chloride and catalytic hydrogenation of the azido group, the resulting trans 7-aminocephem compound (12) was converted to the cis isomer (16) by the established method, involving reduction of the o-nitrobenzenesul-fenimino derivative (14)." @default.
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- W1543282883 date "1980-01-01" @default.
- W1543282883 modified "2023-09-23" @default.
- W1543282883 title "3-Trifluoromethylcephalosporins. I. Total synthesis of tert-butyl (.+-.)-7-amino-3-trifluoromethyl-3-cephem-4-carboxylate." @default.
- W1543282883 doi "https://doi.org/10.1248/cpb.28.62" @default.
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