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

作者：Sorbi Claudia; Prandi Adolfo; Battisti Umberto M; Franchini Silvia; Cornia Andrea; Balzarini Jan; Jeong Lak Shin; Lee Sang Kook; Song Jayoung; Brasili Livio^*

来源：Synlett, 2015, 26(5): 625-630.

DOI：10.1055/s-0034-1380112

• nucleosides
• 1,3-dioxane
• purines
• pyrimidines
• antiviral

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.

• 出版日期2015-3
• 单位河北医科大学