Chemical synthesis of a trisaccharide fragment of a fucosylated glucuronomannan isolated from brown algae

Fucose is abundant in marine organisms, primarily as fucoidan and fucosylated chondroitin sulfate. Our previous study characterized a sulfated and fucosylated glucuronomannan (SFGM) isolated from marine brown algae, exhibiting notable antiviral activity and potential for drug development. Herein, a trisaccharide fragment of this SFGM in the form of [α-L-Fuc(2, 4-diS)]-(1→3)-α-D-Man-(1→4)-α-D-GlcA-OMP was synthesized for the first time. Stereoselective formation of the α-1,2-cis-fucosidic bond was achieved by leveraging solvent effects. The sulfated trisaccharide as the final product, featuring a 2,4-diS-fucose unit and the p-methoxyphenyl group as a pendant at the anomeric position, was successfully accomplished. The synthetic strategy developed in this study offers a foundation for the pharmaceutical development of these SFGM oligosaccharides.