Diastereoselective synthesis of (+/-)-1',4'-dimethyluridine.
The de novo synthesis of racemic 1',4'-dimethyluridine was accomplished in 12 steps starting from 2,5-dimethylfuran and vinylene carbonate. Key steps of the sequence include the stereoconvergent preparation of a meso diacid, and a stereoselective glycosylation without neighboring group participation. Such 1',4'-disubstituted ribonucleoside analogues are undisclosed compounds, which may present interesting biological activities.
Sautrey
Guillaume
G
Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS-UM 1-UM 2 Université Montpellier 2, CC 1705, Place Eugène Bataillon, 34095, Montpellier Cedex 5, France.
Bourgeois
Damien
D
Périgaud
Christian
C
D000438:Alcohols / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis; D006031:Glycosylation; D006536:Heptanes / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry; D006900:Hydroxylation; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013379:Substrate Specificity; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*
C547942:1',4'-dimethyluridine; D000438:Alcohols; D002241:Carbohydrates; D006536:Heptanes; D006571:Heterocyclic Compounds; D014529:Uridine