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.
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.
Kobayashi
Shigeru
S
Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan.
Furukawa
Jun ichi
Ji
Sakai
Tomoko
T
Sakairi
Nobuo
N
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
D005960:Glucosides; D006027:Glycosides; D012117:Resins, Synthetic