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

摘要

The 6-O-mesyl derivative of phenyl 1-thio-#beta#-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 glycopyranosides, 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.