New pyrimidine cyclonucleosides with hydrogenated aglycones: synthesis and X-ray structures.
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.
Shutalev
A D
AD
Department of Organic Chemistry, State Academy of Fine Chemical Technology, Moscow, Russia.
Zavodnik
V E
VE
Gurskaya
G V
GV
D006859:Hydrogen / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009690:Nucleic Acid Conformation; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D014961:X-Ray Diffraction
D011741:Pyrimidine Nucleosides; D006859:Hydrogen