Abstract
Crystalline 1,2-O-(ethane-1,2-diyl)-α-D- glucofuranose (9) is orthorhombic, P 21212, with a = 17.702(4), b = 8.892(2), c = 5.6400(9) Ǻ, Z = 4, R = 0.050, and Rw = 0.041. The conformation of the 1,4-dioxan ring in this bicyclic acetal is slightly distorted from 7C1, and that of the glucofuranose ring is intermediate between the 3E and 3T2 conformations. Extensive intermolecular hydrogen-bonding of exocyclic OH(5) and OH(6) dominates the solid state interactions. In aqueous solution, compound (9) retains close to the same stereochemical characteristics as in the crystal, including those of the exocyclic C(4)-C(5)-C(6) segment of the molecule, according to n.m.r. spectroscopic evidence. These findings provide support for the structures assigned to related bicyclic acetals (7) and (8), which differ from (9) in having a methyl substituent at C(8) on their 1,4-dioxan rings, notably in confirming that the configuration at C(8) is R in (7) and S in (8).
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