Fucosylation of triethyleneglycol-based acceptors into ‘clickable’ α-fucosides

• Glycosylation of l-fucose was achieved with high α-stereoselectivity.
• Glycosylation did not require protecting groups.
• The synthesized fucosides are building blocks for the design of glyconanomaterials.
• Both azido- and alkyne-functionalized fucosides were prepared on gram scale.

Design of multivalent glycoconjugates can find applications such as in anti-adhesive therapy against bacterial infections. Nevertheless, the access to such macromolecules requires functionalized building blocks prepared in a minimum number of steps and on a multi-gram scale at least for the laboratory. Fucose is a representative epitope used by several bacteria for adhesion to their host cells. The stereoselective, rapid, and efficient access to two ‘clickable’ α-fucosides was re-investigated using PPh3/CBr4-promoted glycosylation of chloro- (as precursors of azido-) and alkyne-functionalized triethyleneglycols with fully unprotected l-fucose. The convenient access to such building blocks paves the way to the design of new multivalent glycoconjugates functionalized with fucose epitopes and their applications.

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