Synthesis of N-(2,4-dinitrophenyl) derivatives of D-ribosylamines; unexpected reaction and hydrolysis products

Christopher E. Anson, Josie C. Briggs, Alan H. Haines, Michel Molinier

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Reaction of 2,3-O-isopropylidene-D-ribofuranosylamine with 2,4-dinitrofluorobenzene afforded the crystalline 2,3-O-isopropylidene-N-(2,4-dinitrophenyl)-β-D-ribofuranosylamine (3) and a 1:1 crystalline complex of 2,3-O-isopropylidene-N-(2,4-dinitrophenyl-α-D-ribofuranosylamine and 2,3-O-isopropylidene-β-D-ribofuranose; controlled acidic hydrolysis of 3 afforded N-(2,4-dinitrophenyl-α-D-ribopyranosylamine and not the expected β-D-furanosylamine derivative. The structures of the new compounds were confirmed by NMR spectroscopy and X-ray crystallography.
Original languageEnglish
Article number108564
JournalCarbohydrate Research
Early online date22 Apr 2022
Publication statusPublished - Jun 2022

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