Reductive Cleavage of Carbohydrate p-Toluenesulfonates with Sodium Naphthalene

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Abstract
Carbohydrate p-toluenesulfonates are desulfonylated rapidly and in high yield, by treatment with sodium naphthalene in tetrahydrofuran, to regenerate the original hydroxyl groups. The method has been applied to carbohydrates containing up to three p-toluenesulfonate groups, to unsaturated sugars, and to a nucleoside derivative.

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