Synthesis of naphthoxylosides on solid support

In order to investigate the selective antiproliferative effects shown by 2-(6-hydroxynaphthyl)-β-d-xylopyranoside, the 14 possible β-d-xylopyranosidic compounds were synthesized on solid support. An aminomethylated polystyrene resin was converted into an acid chloride resin and then esterified using dihydroxynaphthalene. The free hydroxy group was then xylosylated under BF3·OEt2 mediated conditions. The xyloside was deprotected and simultaneously cleaved off the resin using NaOMe/MeOH. Final purification using reverse phase HPLC gave the pure xylosides in 6–42% yield with virtually no formation of α-xylosides.