
TY  - JOUR
A1  - Lebuis, AM 
A1  - Lee, DS 
A1  - Perlin, AS 
T1  - 1,2-O-(Ethane-1,2-diyl)-&#945;-D-glucofuranose. Crystal Structure, and the Stereochemistry of Related Bicyclic Acetal Analogues
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1996
VL  - 49
IS  - 3
SP  - 299
EP  - 303
KW  - 
UR  - https://doi.org/10.1071/CH9960299 
N2  - Crystalline 1,2-O-(ethane-1,2-diyl)-&#945;-D- glucofuranose (9) is orthorhombic, P 21212, with a = 17.702(4), b = 8.892(2), c = 5.6400(9) &#506;, 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). 
ER  -

