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

doi:10.1016/j.carres.2022.108564

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

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

17 Downloads (Pure)

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.

Original language	English
Article number	108564
Journal	Carbohydrate Research
Volume	516
Early online date	22 Apr 2022
DOIs	https://doi.org/10.1016/j.carres.2022.108564
Publication status	Published - Jun 2022

Keywords

2,4-Dinitrofluorobenzene derivatives of ribose
Aryl ribofuranosylamines
Covid-19 chemotherapy
Furanose to pyranosyl transition
Nucleoside analogues
Ribofuranosylamine-ribofuranose complex

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@article{fa573c390b9847b2a2e19a3f7857b6a6,

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

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.",

keywords = "2,4-Dinitrofluorobenzene derivatives of ribose, Aryl ribofuranosylamines, Covid-19 chemotherapy, Furanose to pyranosyl transition, Nucleoside analogues, Ribofuranosylamine-ribofuranose complex",

author = "Anson, \{Christopher E.\} and Briggs, \{Josie C.\} and Haines, \{Alan H.\} and Michel Molinier",

note = "Acknowledgements: Part of this work (with JCB) was supported under the MRC AIDS Directed Programme (MRC Grant No 9331372).",

year = "2022",

month = jun,

doi = "10.1016/j.carres.2022.108564",

language = "English",

volume = "516",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier",

}

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 - https://www.scopus.com/pages/publications/85129298013

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 -

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

Abstract

Keywords

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