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■ A Practical Synthetic Method for α- and β-Glycosyloxyacetic Acids

Tadakatsu Mandai,* Hiroshi Okumoto, Tetsuta Oshitari, Katsuyoshi Nakanishi, Katsuhiko Mikuni, Ko-ji Hara, and Ko-zo Hara

*Department of Chemical Technology, Kurashiki University of Science & the Arts, 2640 Nishinoura, Tsurajima-cho, Kurashiki 712-8505, Japan

Abstract

Dihydroxylation of allyl 2,3,4-tri-O-benzyl-6-O-tritylglycosides provides diols, the anomers of which can easily be separated by column chromatography in a practical scale. These anomers can be cleanly transformed into α- and β-glycosyloxyacetic acids, respectively, via oxidative cleavage of the diol followed by oxidation.