The Development of new Methods for the Deoxygenation of Sugars

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Deoxygenation of sugars occupies a significant position in carbohydrate chemistry. Although there have been numerous methods for the deoxygenation via various intermediates, reports of satisfactory methods for the deoxygenation of acetylated sugars, which were often utilized in sugar chemistry, are rare. We have then investigated new efficient routes for the transformation of sugar compounds to deoxysugars.1. Triphenylsilane is a good deoxygenating reagent for the transformation of acetylated sugars to deoxysugars. The deoxygenation has a advantage that the acetylated sugars can be deoxygenated without affecting the other functinalities such as acetals, since the reaction proceeds under neutral conditions.2. p-bis(diphenylhydrosilyl)benzene is a excellent reducing reagent for the deoxygenation of acetylated sugars, since the deoxygenation proceeds completely with less amount of the reducing agent compared with the case of triphenylsilane. Furthermore, the resulting deoxysugars can be easily isolated from the reaction mixture, since the by-products derived from the reagent are high boiling compounds.