title: New pyrimidine cyclonucleosides with hydrogenated aglycones: synthesis and X-ray structures.
abstract: Acid catalysed transformations of (6S)-6,5'-anhydro-6-hydroxy-1-(2',3'-O-isopropylidene-beta-D-ribofuranosyl)hexahydropyrimidine-2-thione are studied. (6R)-6,2'-anhydro-6-hydroxy-1-(alpha-D-ribofuranosyl)hexahydropyrimidine-2-thione was formed as a thermodynamically stable product. Two intermediates, (6S)-6,5'-anhydro-6-hydroxy-1-(beta-D-ribofuranosyl)hexahydropyrimidine-2-thione and 6-hydroxy-1-(D-ribosyl)hexahydropyrimidine-2-thione and products of cleavage of glycosidic bond were identified in the reaction mixtures. Results of X-ray structural determination of the synthesised nucleosides are presented.
authors.affiliation: Department of Organic Chemistry, State Academy of Fine Chemical Technology, Moscow, Russia.
authors.forename: A D
authors.initials: AD
authors.lastname: Shutalev
authors.forename: V E
authors.initials: VE
authors.lastname: Zavodnik
authors.forename: G V
authors.initials: GV
authors.lastname: Gurskaya
mesh_terms: D006859:Hydrogen / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009690:Nucleic Acid Conformation; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D011741:Pyrimidine Nucleosides; D006859:Hydrogen