Synthesis and NMR-analysis of tricyclic nucleosides.
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.
Nielsen
P
P
Department of Chemistry, University of Southern Denmark, 5230 Odense M, Denmark.
Petersen
M
M
Jacobsen
J P
JP
D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D006844:Hydrocarbons, Cyclic; D009705:Nucleosides