Cationic Catalysis Research Articles

3-Deoxyglycosuloses (3-Deoxyglycosones) and the Degradation of Carbohydrates

This chapter discusses the 3-deoxyglycosuloses as intermediates in the formation of metasaccharinic acids by the action of alkali on reducing sugars. The part played by 3-deoxyglycosuloses and their enolic forms, and by unsaturated glycosuloses, in the degradation of carbohydrates dealt, particularly with respect to the formation of 2-furaldehydes. 3-Deoxyglycosuloses are included in the review on dicarbonyl carbohydrates. 3-Deoxy-D-erythro-hexosulose is obtained as a colorless, hygroscopic powder of empirical formula C6H10O5. The compound is soluble in water, methanol, and ethanol, but insoluble in dry acetone, ethyl acetate, and ether. Osazones are readily formed from 3-deoxy-Derythro-hexosulose in the presence or absence of acid. The reactions proceed more rapidly with calcium hydroxide than with sodium hydroxide, and the stereospecificity of the benzilic acid rearrangement appears to be influenced by cationic catalysis, more of the arabino epimer being formed with sodium hydroxide.