A new and versatile synthesis of 1,3-dioxan-5-yl-pyrimidine and purine nucleoside analogues
Sorbi, Claudia × Prandi, Adolfo Battisti, Umberto M. Franchini, Silvia Cornia, Andrea Balzarini, Jan Jeong, Lak Shin Lee, Sang Kook Song, Jayoung Brasili, Livio #
Georg Thieme Verlag
Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry vol:26 pages:625-630
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.