Preparation and diastereomeric separation of an ( S)- and ( R)-1-(methoxycarbonyl)tridec-10-yl glucoside derivative, a precursor for a monosaccharide constituent of resin glycosides

Abstract

The 6- O-mesyl derivative of phenyl 1-thio-β- d-glucopyranoside was prepared from d-glucose as a synthetic equivalent of a 6-deoxy-hexosyl donor. Racemic methyl 11-hydroxytetradecanoate (methyl convolvulinolate) was synthesized by Grignard reaction of propylmagnesium bromide with 10-undecenal followed by hydroboration. Both intermediates were coupled by NIS–TfOH-promoted glycosidation to give a mixture of two diasteromeric glucopyranosides, which were separated on a preparative scale by medium pressure chromatography. One of the products was identified as having the natural ( S)-configuration by comparison of its 1H NMR spectrum with an authentic sample prepared from the corresponding chiral hydroxyfatty acid.