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The [beta]-pyran­ose form, (III), of 3-deoxy-D-ribo-hexose (3-deoxy-D-glucose), C6H12O5, crystallizes from water at 298 K in a slightly distorted 4C1 chair conformation. Structural analyses of (III), [beta]-D-glucopyran­ose, (IV), and 2-deoxy-[beta]-D-arabino-hexopyran­ose (2-deoxy-[beta]-D-glucopyran­ose), (V), show significantly different C-O bond torsions involving the anomeric carbon, with the H-C-O-H torsion angle approaching an eclipsed conformation in (III) (-10.9°) compared with 32.8 and 32.5° in (IV) and (V), respectively. Ring carbon deoxy­genation significantly affects the endo- and exocyclic C-C and C-O bond lengths throughout the pyran­ose ring, with longer bonds generally observed in the monodeoxy­genated species (III) and (V) compared with (IV). These structural changes are attributed to differences in exocyclic C-O bond conformations and/or hydrogen-bonding patterns superimposed on the direct (intrinsic) effect of monodeoxy­genation. The exocyclic hydroxy­methyl conformation in (III) (gt) differs from that observed in (IV) and (V) (gg).
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