Degradation of Carbohydrates. II. The Action of Acid and Alkali on 3-Deoxyhexosones

Abstract

The two 3-deoxy-D-hexosones, 3-deoxy-D-erythrohexosone and 3-deoxy-D-threohexosone, were quantitatively converted by acid to 5-(hydroxymethyl)-2-furaldehyde.The mechanism of the formation of 2-furaldehyde from sugars is discussed. Calcium hydroxide rapidly converted 3-deoxy-D-erythrohexosone to α- and β-glucometasaccharinic acids, and 3-deoxy-D-threohexosone to α- and β-galactometasaccharinic acids.