title: Synthesis of 2',3'-dideoxy-2'-monofluoromethyl azanucleosides.
abstract: (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.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 354 Fenglin Lu, Shanghai 200032, China.
authors.forename: Xiao-Long
authors.initials: XL
authors.lastname: Qiup
authors.forename: Feng-Ling
authors.initials: FL
authors.lastname: Qing
mesh_terms: D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D009690:Nucleic Acid Conformation
chemical_list: D015224:Dideoxynucleosides