The selective cleavage of permethylated glycopyranosiduronic acid linkages by oxidative decarboxylation with lead tetraacetate

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Abstract
Reaction of permethylated glycopyranosiduronic acids with lead tetraacetate furnishes epimeric 5-acetoxypentopyranosides as products of oxidative decarboxylation. Glycoside cleavage then occurs on treatment with sodium borohydride which affords the corresponding pentitols with exposure of aglyconic hydroxyl groups. The reaction sequence has been performed with permethylated derivatives of methyl β-melibiosiduronic acid, methyl β-gentiobiosiduronic acid, gum arabic, leiocarpan A, Sterculia urens gum, and citrus pectic acid. The scope of the reaction sequence in polysaccharide studies is discussed.

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