Stereochemically controlled transformations related to pyrimidine nucleosides and their analogues

The diastereoisomeric differentiations and anomerizations of 5,6-dihydrothymidine and its anhydro derivatives were studied. In particular, the oxetane ring opening of (5S)-1-(3,5-anhydro-2-deoxy-beta-D-threopentofuranosyl)-5,6-dihydr othymine under acid catalysed conditions substantiated a number of the configurational modifications at the sugar moiety. The 1,3-dipolar cycloaddition to the pyrimidine C(5), C(6)-double bond was intramolecularly facilitated by the activation of 1-(3-azido-2-hydroxypropyl)uracil. (E)- and (Z)-1-Prop-enyl- and properly functionalized 1-propyl-uracil derivatives were also prepared and used for the synthesis of the tetrahydro-oxazolo[3,2-c]pyrimidine-5,6-(4H, 6H)dione and 9,3'-cyclo-3-propyl (or prop-1-enyl)-8-azaxanthine derivatives.