The sugar trehalose is known to play a central role in the desiccation tolerance of many organisms. Essential to trehalose's role are its glass forming abilities and ability to directly interact with lipid molecules. Detailed information on the structure and dynamics of glassy trehalose and its interactions with lipids, however, have been elusive. We have used solid-state NMR and ab initio quantum mechanical methods (Gaussian 94) in order to characterize the possible molecular conformations of trehalose. Using a simplified structure (2-(tetrahydropyran-2-yloxy) tetrahydropyran) as a model we have calculated the energy and 13C magnetic shielding parameters as a function of the two glycosidic torsion angles. Combining ab initio derived maps and using the 13C lineshape as constraints we were able to construct the torsion angle distribution map for alpha-alpha' trehalose. We believe measurements of 13C isotropic chemical shift and other solid-state NMR tensor parameter distributions in combination with ab initio methods can prove useful in identifying sources of structural disorder in glassy trehalose. By monitoring these structural distributions new information about the membrane surface associative properties of trehalose and other sugars should be accessible.