title: 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-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 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.
authors.affiliation: Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan.
authors.forename: Shigeru
authors.initials: S
authors.lastname: Kobayashi
authors.forename: Jun ichi
authors.initials: Ji
authors.lastname: Furukawa
authors.forename: Tomoko
authors.initials: T
authors.lastname: Sakai
authors.forename: Nobuo
authors.initials: N
authors.lastname: Sakairi
mesh_terms: D002240:Carbohydrate Sequence; D005960:Glucosides / Q000138:chemical synthesis* / Q000302:isolation & purification; D006027:Glycosides / Q000138:chemical synthesis; D008969:Molecular Sequence Data; D012117:Resins, Synthetic / Q000138:chemical synthesis
chemical_list: D005960:Glucosides; D006027:Glycosides; D012117:Resins, Synthetic