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First synthesis of 1-deazacytidine, the C-nucleoside analogue of cytidine

First synthesis of 1-deazacytidine, the C-nucleoside analogue of cytidine
First synthesis of 1-deazacytidine, the C-nucleoside analogue of cytidine
The synthesis of 1-deazacytidine, the C-nucleoside analogue of cytidine, is described. It involves coupling of a protected 2-amino-5-bromopyridine with perbenzylated ribonolactone and transformation of the pyridine ring into the desired substituted pyridone. This synthesis completes the family of C-nucleosidic analogues of natural nucleosides.
glycosides, chemistry, pyridine
0040-4039
3121-3123
Sollogoub, M.
0f6829b1-2f62-40c8-bfa1-cab69c36b694
Fox, K. R.
9da5debc-4e45-473e-ab8c-550d1104659f
Powers, V. E. C.
e7349208-15d4-492c-ad88-ff8f2eeea52a
Brown, T.
a64aae36-bb30-42df-88a2-11be394e8c89
Sollogoub, M.
0f6829b1-2f62-40c8-bfa1-cab69c36b694
Fox, K. R.
9da5debc-4e45-473e-ab8c-550d1104659f
Powers, V. E. C.
e7349208-15d4-492c-ad88-ff8f2eeea52a
Brown, T.
a64aae36-bb30-42df-88a2-11be394e8c89

Sollogoub, M., Fox, K. R., Powers, V. E. C. and Brown, T. (2002) First synthesis of 1-deazacytidine, the C-nucleoside analogue of cytidine. Tetrahedron Letters, 43 (17), 3121-3123. (doi:10.1016/S0040-4039(02)00481-1).

Record type: Article

Abstract

The synthesis of 1-deazacytidine, the C-nucleoside analogue of cytidine, is described. It involves coupling of a protected 2-amino-5-bromopyridine with perbenzylated ribonolactone and transformation of the pyridine ring into the desired substituted pyridone. This synthesis completes the family of C-nucleosidic analogues of natural nucleosides.

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More information

Published date: 22 April 2002
Keywords: glycosides, chemistry, pyridine
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Identifiers

Local EPrints ID: 19860
URI: http://eprints.soton.ac.uk/id/eprint/19860
DOI: doi:10.1016/S0040-4039(02)00481-1
ISSN: 0040-4039
PURE UUID: d2b17561-15ce-4833-9c23-effad6622b67
ORCID for K. R. Fox: ORCID iD orcid.org/0000-0002-2925-7315

Catalogue record

Date deposited: 17 Feb 2006
Last modified: 16 Mar 2024 02:36

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Contributors

Author: M. Sollogoub
Author: K. R. Fox ORCID iD
Author: V. E. C. Powers
Author: T. Brown

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