Synthesis of oxidized methyl 4-O-methyl-β-d-glucopyranoside and methyl β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside derivatives as substrates for fluorescence labeling reactions Original Research Article

The synthetic cellulose model compounds methyl 4-O-methyl-β-d-glucopyranoside and methyl 4-O-methyl-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside and related 6-O-protected intermediates were oxidized in good to fair yields using Swern-conditions or bromine/bis(tributyltin) oxide, respectively, to afford compounds containing 6-aldehyde, 3-keto, and 2,3-diketo groups. Cellobiose and oxidized monosaccharides were then labeled with the carbonyl-selective fluorescence marker 9-(7-amino-1,4,7-trioxaheptyl)-9H-carbazolecarboxamide (CCOA). The labeled derivatives serve as model compounds for the determination of minute amounts of carbonyl groups in cellulosic polysaccharides.