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

…, VK Belsky, AI Stash, VE Zavodnik, PJ Stang

Index: Brel, Valery K; Belsky, Vitaly K; Stash, Adam I; Zavodnik, Valery E; Stang, Peter J Organic and biomolecular chemistry, 2003 , vol. 1, # 23 p. 4220 - 4226

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Citation Number: 16

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 ...