Solved: Gentiobiose, a rare disaccharide found in saffron and gentian, is a reducing

Chapter 25, Problem 25.48

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Gentiobiose, a rare disaccharide found in saffron and gentian, is a reducing sugar and forms only d-glucose on hydrolysis with aqueous acid. Reaction of gentiobiose with iodomethane and Ag2O yields an octamethyl derivative, which can be hydrolyzed with aqueous acid to give 1 equivalent of 2,3,4,6-tetraO-methyl-d-glucopyranose and 1 equivalent of 2,3,4-tri-O-methyl-d-glucopyranose. If gentiobiose contains a b-glycoside link, what is its structure?

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