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- Title
Synthesis, Structure, and Conformational Analysis of Nucleoside Analogues Comprising Six-Membered 1,3-Oxathiane Sugar Rings.
- Authors
Abou Assi, Hala; Martínez‐Montero, Saúl; Dixit, Dilip M.; Chua, Zhijie; Bohle, D. Scott; Damha, Masad J.
- Abstract
We report on the synthesis, characterization, and conformational analysis of 1,3-oxathiane nucleosides of both pyrimidine and purine nucleobases. The novel nucleoside analogues were prepared from readily available starting materials as α/β anomeric mixtures. The purine nucleosides were obtained as separable N7/N9 regioisomers. The structures were identified by extensive NMR analysis. The X-ray structure of the N7-β-OMe-purine nucleoside analogue 16 shows that the 1,3-oxathiane sugar ring adopts a perfect chair conformation with both the hydroxymethyl and the nucleobase placed in equatorial positions.
- Subjects
NUCLEOSIDES; PYRIMIDINE synthesis; CHEMICAL synthesis; PURINE synthesis; NUCLEAR magnetic resonance
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 9, p1945
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201403642