TY - JOUR
T1 - Synthesis of N-(2,4-dinitrophenyl) derivatives of D-ribosylamines; unexpected reaction and hydrolysis products
AU - Anson, Christopher E.
AU - Briggs, Josie C.
AU - Haines, Alan H.
AU - Molinier, Michel
N1 - Acknowledgements: Part of this work (with JCB) was supported under the MRC AIDS Directed Programme (MRC Grant No 9331372).
PY - 2022/6
Y1 - 2022/6
N2 - 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.
AB - 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.
KW - 2,4-Dinitrofluorobenzene derivatives of ribose
KW - Aryl ribofuranosylamines
KW - Covid-19 chemotherapy
KW - Furanose to pyranosyl transition
KW - Nucleoside analogues
KW - Ribofuranosylamine-ribofuranose complex
UR - http://www.scopus.com/inward/record.url?scp=85129298013&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2022.108564
DO - 10.1016/j.carres.2022.108564
M3 - Article
SN - 0008-6215
VL - 516
JO - Carbohydrate Research
JF - Carbohydrate Research
M1 - 108564
ER -