A very efficient synthesis of a mannosyl orthoester [2]rotaxane and mannosidic [2]rotaxanes.
The direct preparation of mannosyl[2]rotaxane derivatives by O-glycosylation from tetra-O-acetyl-alpha-D-mannosyltrichloroacetimidate and a tert-butylanilinium alcohol in the presence of dibenzo-24-crown-8 is described. The method appears to be very efficient and allows for the preparation of either orthoester or mannosyl rotaxane derivatives, depending on reaction conditions.
Coutrot
Frédéric
F
Institut des Biomolécules Max Mousseron, UMR 5247CNRS-Universités Montpellier 2 et 1, Bâtiment de Recherche Max Mousseron, Ecole Nationale Supérieure de Chimie de Montpellier, 34296 Montpellier Cedex 5, France. frederic.coutrot@univ-moutp2.fr
Busseron
Eric
E
Montero
Jean-Louis
JL
D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D008362:Mannosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D043862:Rotaxanes / Q000138:chemical synthesis* / Q000737:chemistry
D006027:Glycosides; D008362:Mannosides; D043862:Rotaxanes