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

Anson, Christopher E., Briggs, Josie C., Haines, Alan H. and Molinier, Michel (2022) Synthesis of N-(2,4-dinitrophenyl) derivatives of D-ribosylamines; unexpected reaction and hydrolysis products. Carbohydrate Research, 516. ISSN 0008-6215

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Abstract

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.

Item Type: Article
Additional Information: Acknowledgements: Part of this work (with JCB) was supported under the MRC AIDS Directed Programme (MRC Grant No 9331372).
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: LivePure Connector
Date Deposited: 05 Jul 2022 14:30
Last Modified: 24 Sep 2022 18:41
URI: https://ueaeprints.uea.ac.uk/id/eprint/85963
DOI: 10.1016/j.carres.2022.108564

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