3-Deoxy-D-fructose

The title compound, 3-deoxy-D-erythro-hexulose (3-deoxy-D-fructose), C₆H₁₂O₅, crystallizes from ethanol as the β-D-pyranose form in the ²C₅ conformation. Significant differences from β-D-fructopyranose (D-fructose) are observed in the hydrogen-bonding scheme. The primary hydroxyl group is hydrogen bonded internally to the ring oxygen in D-fructose, while it forms an intermolecular bond to the analogous oxygen of another molecule in the 3-deoxy analog. In both molecules, the hydroxyl group attached to anomeric carbon is a strong hydrogen-bond donor; it is also a hydrogen-bond acceptor in D-fructose, but not in 3-deoxy-D-fructose.

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