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-β-D-ribofuranosyl)hexahydropyrimidine-2-thione are studied. (6R)-6,2′-anhydro-6-hydroxy-1-(α-D-ribofuranosyl)hexahydropyrimidine-2-thione was formed as a thermodynamically stable product. Two intermediates, (6S)-...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2000-10, Vol.19 (10-12), p.1831-1846
Main Authors: Shutalev, Anatoly D., Zavodnik, Valeriy E., Gurskaya, Galina V.
Format: Article
Language:English
Subjects:
Hydrogen - chemistry
Magnetic Resonance Spectroscopy
Nucleic Acid Conformation
Pyrimidine Nucleosides - chemical synthesis
Pyrimidine Nucleosides - chemistry
X-Ray Diffraction
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Summary:Acid catalysed transformations of (6S)-6,5′-anhydro-6-hydroxy-1-(2′,3′-O-isopropylidene-β-D-ribofuranosyl)hexahydropyrimidine-2-thione are studied. (6R)-6,2′-anhydro-6-hydroxy-1-(α-D-ribofuranosyl)hexahydropyrimidine-2-thione was formed as a thermodynamically stable product. Two intermediates, (6S)-6,5′-anhydro-6-hydroxy-1-(β-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.
ISSN:1525-7770
1532-2335
DOI:10.1080/15257770008045464