Intramolecular glycosylation to form 4-methoxy-2,6-dioxopyrimidine nucleosides via O6,5'-cyclonucleosides

Nucleosides Nucleotides. 1999 Nov-Dec;18(11-12):2415-23. doi: 10.1080/07328319908044616.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Glycosylation
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry

Substances

  • Nucleosides