Stereoselective Syntheses of α-Glucuronides Using Dehydrative Glycosylation

Article abstract of DOI:10.1246/bcsj.69.3247

Methyl and benzyl 2,3,4-tri-O-benzyl-D-glucopyranuronates, prepared from D-glucurono-6,3-lactone, afforded selectively the corresponding α-glucopyranosiduronates by the aid of the condensing reagent system composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine. Using this method, O-α-D-glucopyranuronosyl-(1→3)-O-α-L-arabinofuranosyl- (1→3)-D-xylopyranose, one of the minimal component units in the structure of plantago-mucilage A from the seeds of Plantago asiatica Linne constituting a Chinese medicine : chegianzi [HU~P].