1027205-48-6Relevant academic research and scientific papers
Enantioselective Synthesis and Conformational Study of Cyclohexene Carbocyclic Nucleosides
Wang, Jing,Herdewijn, Piet
, p. 7820 - 7827 (2007/10/03)
Enantioselective synthesis of a new family of unsaturated six-membered carbocyclic nucleosides using (R)-(-)-carvone as starting material is described. Introduction of the base moiety via Mitsunobu reaction proceeded regio- and stereoselectively and with good chemical yield, while the Pd-coupling approach failed. 1H NMR study and molecular modeling show the adenine compound exists in an equilibrium of 3H2 and 2H3 conformers (ratio 7:3) in favor of the 3′-endo half-chair conformation, with the base oriented in a pseudoaxial position. This conformational preference can be explained by the π→σ*C1′-N1 interaction involving the antibonding orbital of the C1′-N bond.
