Versatile synthesis of rare nucleotide furanoses.
Direct activation of unprotected thioimidoyl furanosides yielded in only one step and few minutes a panel of rare uridine 5'-diphospho-furanoses. Diastereoselectivity of the reaction was tightly connected with reaction time, temperature, and nature of the furanosyl donor. This approach was totally selective since no ring expansion from the initial five-membered ring to the more stable pyranose form was observed.
Peltier
Pauline
P
Ecole Nationale Supérieure de Chimie de Rennes, Organic and Supramolecular Chemistry, CNRS, Avenue du Général Leclerc, F-35700 Rennes.
Daniellou
Richard
R
Nugier-Chauvin
Caroline
C
Ferrières
Vincent
V
D007096:Imidoesters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010766:Phosphorylation; D013438:Sulfhydryl Compounds / Q000737:chemistry; D014529:Uridine / Q000737:chemistry; D014530:Uridine Diphosphate / Q000737:chemistry
D007096:Imidoesters; D009711:Nucleotides; D013438:Sulfhydryl Compounds; D014530:Uridine Diphosphate; D014529:Uridine