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Synthesis and NMR-analysis of tricyclic nucleosides
P Nielsen1, M Petersen, J P Jacobsen
1Department of Chemistry, University of Southern Denmark, 5230 Odense M, Denmark.
Nucleosides, Nucleotides & Nucleic Acids
|September 21, 2001
Abstract:
Two anomeric tricyclic nucleosides have been synthesised from diacetone-D-glucose using oxidation, stereoselective Grignard-addition of a vinyl-group, a stereoselective dihydroxylation followed by a tandem ring closing reaction, and finally a nucleobase coupling. The main beta-configured product was examined and its configuration confirmed using NMR-spectroscopy in connection to ab initio calculations. The preferred conformation of this tricyclic nucleoside was described.