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

Gérald Enderlin (1) , Claude Taillefumier (2) , Claude Didierjean (3) , Yves Chapleur (1)

1 SRSMC - Structure et Réactivité des Systèmes Moléculaires Complexes
2 SEESIB - Synthèse et étude de systèmes à intêret biologique
3 SFL - Structures Formelles du Langage

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 Mitsututed conditions to provide it new Family of fused-ring analogues of uridine nucleoside in which the N-1 nitrogen atom is embedded in an amino sugar ring. An analogue of uridine of D-1 ibo configuration is prepared.

Domaines: Chimie

Gérald Enderlin, Claude Taillefumier, Claude Didierjean, Yves Chapleur. An efficient route to acyclic C-nucleosides and fused-ring analogues of uridine from exo-glycals. Journal of Organic Chemistry, 2009, 74 (21), pp.8388-8391. ⟨10.1021/jo901604w⟩. ⟨hal-00435725⟩