5′-Chloro-5′-deoxy-2′,3′-O-isopropylidene-6-fluoro nebularine

Abstract

In this paper, we report on the synthesis and spectroscopic characterization of the novel nucleoside 5 -chloro-5 -deoxy-2 ,3 -O-isopropylidene-6-fluoro nebularine, obtained as a side product during the second step of the synthesis of 5 -fluoro-5 -deoxy-5-aminoimidazole-4-carboxamide-β-driboside (5 -F-AICAR), a non-phosphorylable analogue of 5-aminoimidazole-4-carboxamide-β-driboside (AICAR).

Editorial: Special Issue “Molecules from Side Reactions”

“…In the third paper, the authors described the access to the rare d-and l-psicose derivatives via hydroxy methylation of the ribono lactone [3]. The fourth paper dealt with the synthesis of an intriguing side product obtained during the 5 -ribose fluorination of the nucleoside 6-chloropurine riboside [4]. This reaction occurred during the preparation of a valuable, more lipophilic, analogue of the imidazo-nucleoside AICAR [5].…”