Regioselective 3-O-Substitution of Unprotected Thiodigalactosides: Route to Specific Galectin Inhibitors

Tomáš Vašíček, Vojtěch Spiwok, Jakub Červený, Lucie Petrásková, Ladislav Bumba, Helena Pelantová, Vladimír Křen & Pavla Bojarová
Regioselective derivatization of oligosaccharides is a challenging issue in carbohydrate chemistry. A commonly required series of (de)protection steps substantially lowers synthetic yields and increases time demands. We present here a regioselective one-step introduction of benzylic substituents at 3-hydroxy moieties of beta-D-galactopyranosyl-(11)-thio-beta-D-galactopyranoside (TDG) employing tin butyl oxide in fair isolated yields. These glycomimetics act as inhibitors of galectins - human lectins, which are biomedically attractive targets for therapeutic inhibition. The affinity of prepared glycomimetics to recombinant...
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