SYNTHESIS AND LIPASE-CATALYZED RESOLUTION OF 5-(HYDROXYMETHYL)-1,3-DIOXOLAN-4-ONES - MASKED GLYCEROL ANALOGS AS POTENTIAL BUILDING-BLOCKS FOR PHARMACEUTICALS

(Hydroxymethyl)-1,3-dioxolan-4-ones from mandelic and lactic acids and 1,5,5-trimethyl-3-phenyloxazolidin-2-one from mandelamide were alpha- alkylated using benzyl chloromethyl ether. Reductive debenzylation of the products of alkylation unmasked the hydroxymethyl groups. The comp ounds obtained in this fashion were subsequently subjected to lipase-c atalyzed resolution in organic media. Depending on the lipase and subs trate employed, enantiomeric ratios up to E = 200 were observed. The o btained optically pure compounds can be considered as masked 2-substit uted glycerol equivalents, which could be used for the preparation of tertiary (aryloxy)propanolamines, compounds having potential beta-bloc king activity.