Intramolecular glycosylation to form 4-methoxy-2,6-dioxopyrimidine nucleosides via O6,5'-cyclonucleosides.
Lewis-acid promoted intramolecular N1 glycosylation to form the novel O6,5'-cyclonucleoside 1a occurs in high yield from the corresponding acyclic thiophenyl-glycoside 12. The relative stability of the O6,5' tether compared with O2,5' and O2,3' tethers is reported. Cleavage of the anhydro bond was effected with aqueous base to yield the 4-methoxybarbituric acid nucleoside analogue 14.
Castro
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Department of Chemistry, University of San Francisco, CA 94117-1080, USA.
Chen
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Jung
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ME
D006031:Glycosylation; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D009705:Nucleosides