1,3-Dioxan-5-yl pyrimidine and purine nucleoside analogues were prepared following a new and versatile synthetic strategy. These analogues were synthesized via nucleophilic addition of the selected nucleobase to a 1,3-dioxane scaffold that presents an appropriate leaving group in position 5. In particular cis and trans isomers of purine/pyrimidine nucleosides and their halogenated homologues were obtained. NMR experiments, carried out on the cis isomers, led to assignment of an equatorial orientation to the 2-hydroxymethyl group and axial orientation to the nucleobase in position 5 of the 1,3-dioxane. The trans isomers showed a diequatorial orientation of these groups. These assignments were confirmed by X-ray crystallographic studies

A New and Versatile Synthesis of 1,3-Dioxan-5-yl-pyrimidine and Purine Nucleoside Analogues / Sorbi, Claudia; Prandi, Adolfo; Battisti, UMBERTO MARIA; Franchini, Silvia; Cornia, Andrea; Balzarini, Jan; Jeong, Lak Shin; Lee, Sang Kook; Song, Jayoung; Brasili, Livio. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 26:5(2015), pp. 625-630. [10.1055/s-0034-1380112]

A New and Versatile Synthesis of 1,3-Dioxan-5-yl-pyrimidine and Purine Nucleoside Analogues

SORBI, Claudia;PRANDI, adolfo;BATTISTI, UMBERTO MARIA;FRANCHINI, Silvia;CORNIA, Andrea;BRASILI, Livio
2015

Abstract

1,3-Dioxan-5-yl pyrimidine and purine nucleoside analogues were prepared following a new and versatile synthetic strategy. These analogues were synthesized via nucleophilic addition of the selected nucleobase to a 1,3-dioxane scaffold that presents an appropriate leaving group in position 5. In particular cis and trans isomers of purine/pyrimidine nucleosides and their halogenated homologues were obtained. NMR experiments, carried out on the cis isomers, led to assignment of an equatorial orientation to the 2-hydroxymethyl group and axial orientation to the nucleobase in position 5 of the 1,3-dioxane. The trans isomers showed a diequatorial orientation of these groups. These assignments were confirmed by X-ray crystallographic studies
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A New and Versatile Synthesis of 1,3-Dioxan-5-yl-pyrimidine and Purine Nucleoside Analogues / Sorbi, Claudia; Prandi, Adolfo; Battisti, UMBERTO MARIA; Franchini, Silvia; Cornia, Andrea; Balzarini, Jan; Jeong, Lak Shin; Lee, Sang Kook; Song, Jayoung; Brasili, Livio. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 26:5(2015), pp. 625-630. [10.1055/s-0034-1380112]
Sorbi, Claudia; Prandi, Adolfo; Battisti, UMBERTO MARIA; Franchini, Silvia; Cornia, Andrea; Balzarini, Jan; Jeong, Lak Shin; Lee, Sang Kook; Song, Jayoung; Brasili, Livio
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