An efficient route to acyclic C-nucleosides and fused-ring analogues of uridine from exo-glycals.
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.
UMR SRSMC 7565 Nancy-Université CNRS, Groupe SUCRES, BP 239, F-54506 Vandoeuvre, France.
Gérald
G
Enderlin
Claude
C
Taillefumier
Claude
C
Didierjean
Yves
Y
Chapleur
D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D014529:Uridine / Q000737:chemistry*
D009705:Nucleosides; D014529:Uridine