Esters of arylpropionic acids with 1,2:5,6-di-O-isopropylidene- and 1,2-O-isopropylidene-α-D-glucofuranose

Abstract

On fractional crystallization of 3-O-(2-(2-fluoro-4-biphenylyl)propionyl)-, 3-O-(2-(4-isobutylphenyl)propionyl)- and 3-O-(2-(6-methoxy-2-naphthyl)propionyl)-1,2 :5,6-di-O-isopropylidene-α-D-glucofuranoses V-VII optically pure R-diastereoisomers were isolated. The derivatives of 1,2-O-isopropylidene-α-D-glucofuranose obtained on partial deacetylation of esters V-VII were separated chromatographically to R and S-diastereoisomers. Their hydrolysis or transesterification afforded optically pure arylpropionic acids or their methyl esters, respectively. Kinetic resolution of the acids gives rise to esters V-VII enriched in R-diastereoisomer.