Synthesis of 2′,3′-dideoxy-2′-monofluoromethyl azanucleosides Original Research Article

(2S,4S)-Methyl-N-tert-butoxycarbonyl-4-monofluoromethylpyroglutamate 6 was synthesized via a key dehydrofluorination followed by hydrogenation. Compound 6 was converted to (5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-pyrrolidone 12 over four steps in 62% yield, which was used as a precursor for the synthesis of 2′,3′-dideoxy-2′-monofluoromethyl azanucleosides 17–18.