Regioselective enzymatic acylation of ribavirin to give potential multifunctional derivatives

Lipase-catalyzed synthesis of potential multifunctional ribavirin derivatives was performed in acetone. Divinyl dicarboxylates with different chain lengths (C₄, C₆, C₉, C₁₀) were used as acyl donors and the reactions were catalyzed by lipase immobilized on acrylic resin from Candida antarctica (CAL-B). Ribavirin was regioselectivly acylated at the primary hydroxyl groups and the corresponding vinyl esters (C₄, C₆, C₉, C₁₀) were prepared in respective yields of 48%, 65%, 54%, 55%.