An efficient route to acyclic C-nucleosides and fused-ring analogues of uridine from exo-glycals.

ABSTRACT

Beta-amino esters prepared from activated exo-glycals are transformed into acyclic C-nucleoside with a C-4-substituted uracil derivative that can be cyclized under Mitsunobu conditions to provide a new family of fused-ring analogues of uridine nucleoside in which the N-1 nitrogen atom is embedded in an imino sugar ring. An analogue of uridine of D-ribo configuration is prepared.