Open-Air Stereoselective Synthesis of C-Aryl Fucosides/Arabinosides

An open-air stereoselective preparation of C-aryl fucosides and arabinosides was reported using 3,4-O-carbonate glycals and arylboronicic acids based on a palladium-catalyzed decarboxylative allylation at ambient conditions and the configurations of products were determined by NMR, HRMS and X-ray single crystal diffraction analysis. Competitive reactions indicated that this approach has good compatibility with amino and alcoholic/phenolic hydroxyl groups. Further functionlization of unsaturated C-glycosides can be used to prepare a variety of C-glycosides. This mild method is simple in operation, wide application in substrate range, which provides a new idea for the rapid construction of carbohydrate library.

Automated summary

An open-air stereoselective preparation of C-aryl fucosides and arabinosides was reported using 3,4-O-carbonate glycals and arylboronic acids. The configurations of products were determined by various analytical techniques. Competitive reactions demonstrated the compatibility of this method and its potential for the preparation of various C-glycosides through functionalization.