The synthesis of some fluoro derivatives of sucrose.
2,3,1',3'4',6'-Hexa-O-benzylsucrose was obtained by mild acid-catalysed hydrolysis of the 4,6-O-isopropylidene derivative and then converted into its 4,6-di-O-mesyl derivative. Selective displacement of this disulphonate with fluoride anion (from tetrabutylammonium fluoride) then afforded the 6-fluoro-4-mesylate. Removal of the protecting groups yielded 6-deoxy-6-fluorosucrose, which was characterised as its crystalline hepta-acetate. A derivative of 6-deoxy-6-fluoro-galacto-sucrose was formed when the above 6-fluoro-4-mesylate was subjected to nucleophilic displacement with benzoate anion.
D055598:Chemical Phenomena; D002621:Chemistry; D005459:Fluorides; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013549:Sweetening Agents
D013549:Sweetening Agents; D013395:Sucrose; D005459:Fluorides