156386-24-2Relevant academic research and scientific papers
The Synthesis and Conformation of 2'- and 3'-Hypermodified Tricyclic Nucleosides and Their Use in the Synthesis of Novel 2'- or 3'-Isomeric 4(7)-Substituted Isoxazolidine-nucleosides
Rong, J.,Roselt, P.,Plavec, J.,Chattopadhyaya, J.
, p. 4921 - 4936 (2007/10/02)
Intramolecular 1,3-dipolar cycloaddition reactions of a number of C-alkenyl nitrones of nucleoside derivatives 7, 9, 19 and 28 afforded 2'- and 3'-hypermodified tricyclic nucleoside derivatives 10 (56percent), 11 (43percent), 20 (91percent) and 29 (75percent), respectively.The solution structures of these tricyclic nucleoside derivatives have been investigated using the 3JHH (1H at 500 MHz) and the NMR-derived torsion angle constrained energy minimizations with the aid of MacroModel's AMBER force field.Subsequent Tamao oxidation of the hypermodified nucleoside derivatives 20 and 29 gave spiro-4(7)-substituted isoxazolidine-nucleoside derivatives 21 and 30, respectively.
