Title: A new and versatile synthesis of 1,3-dioxan-5-yl-pyrimidine and purine nucleoside analogues
Authors: Sorbi, Claudia ×
Prandi, Adolfo
Battisti, Umberto M.
Franchini, Silvia
Cornia, Andrea
Balzarini, Jan
Jeong, Lak Shin
Lee, Sang Kook
Song, Jayoung
Brasili, Livio #
Issue Date: Mar-2015
Publisher: Georg Thieme Verlag
Series Title: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry vol:26 pages:625-630
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.
ISSN: 0936-5214
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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