New short route to unsaturated fluoroketonucleosides: case of 5-fluoro-1-(6-O-acetyl-3,4-di-deoxy-3-fluoro-beta-D-glycero-hex-3-eno-pyranos-2-ulosyl) uracil.
The proposed short synthesis involves two key steps: Oxidation of the isopropylidene derivative of the 3-fluoronucleoside possessing a free hydroxyl group in 2-position and acetylation of deprotected 3-fluoro-2-ketonucleoside which, after a beta-elimination reaction, gives the desired unsaturated ketonucleoside 5.
Egron
Marie-José
MJ
Ecole Nationale Supérieure de Chimie de Paris, CNRS-UMR 8151, 11, Rue P. et M. Curie, Paris 75005, France.
Komiotis
Dimitri
D
Dorange
Ismet
I
Herscovici
Jean
J
Ollapally
Abraham P
AP
Antonakis
Kostas
K
D002855:Chromatography, Thin Layer; D005461:Fluorine / Q000737:chemistry*; D005472:Fluorouracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D007166:Immunosuppressive Agents / Q000494:pharmacology; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis
C503849:5-fluoro-1-(6-O-acetyl-3,4-di-deoxy-3-fluoro-beta-D-glycero-hex-3-eno-pyranos-2-ulosyl) uracil; D007166:Immunosuppressive Agents; D007659:Ketones; D009705:Nucleosides; D005461:Fluorine; D014498:Uracil; D005472:Fluorouracil