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Issue 23, 2003
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Synthesis and molecular structure of new acyclic analogues of nucleotides with a 1,2-alkadienic skeleton

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Abstract

Reaction of 1-chloro-4-(diethoxyphosphonyl)alka-2,3-dienes 14,15 with purine and pyrimidine heterocyclic bases in the presence of cesium carbonate afforded new acyclic analogues of nucleotides containing a 1,2-alkadienic skeleton 18–23. Dealkylation of 18–23 furnished phosphonic acids 2a–f. In contrast, alkylation reaction with 1-chloro-4-(diethoxyphosphonyl)octa-2,3-diene 16 led to Z- and E- 1,3-alkadienic phosphonates 25a,b and 26a,b. A similar reaction with 1-chloro-4-(diethoxyphosphonyl)-2-methylbuta-2,3-diene 17 led to the elimination of hydrochloride and formation of 4-(diethylphosphonyl)-2-methylbut-1-en-3-yne 24. Molecular structures of new acyclic nucleotides 18 and 2f are determined by X-ray crystallographic analysis.

Graphical abstract: Synthesis and molecular structure of new acyclic analogues of nucleotides with a 1,2-alkadienic skeleton

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Supplementary files

Article information


Submitted
15 Aug 2003
Accepted
06 Oct 2003
First published
27 Oct 2003

Org. Biomol. Chem., 2003,1, 4220-4226
Article type
Paper

Synthesis and molecular structure of new acyclic analogues of nucleotides with a 1,2-alkadienic skeleton

V. K. Brel, V. K. Belsky, A. I. Stash, V. E. Zavodnik and P. J. Stang, Org. Biomol. Chem., 2003, 1, 4220
DOI: 10.1039/B309684J

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