X-ray and 1H nmr analyses of 5-(m-benzyloxybenzyl)-1-[(1,3-dihydroxy-2-propoxy)methyl]uracil, an acyclonucleoside inhibitor of uridine phosphorylase

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Abstract
The title compound crystallizes in the triclinic space group P.hivin.1 and the cell dimensions are a = 16.890(3), b = 9.586(2), c = 6.316(1) .ANG., .alpha. = 91.09(1), .beta. = 93.50(1), .gamma. = 93.04(1).degree.. X-ray intensity data were measured on a diffractometer, and the crystal structure was determined by direct methods. Least-squares refinement, which included all hydrogen atoms, converged at R = 0.056 for 3454 observed reflections. Adjacent six-membered rings are approximately perpendicular to one another. The glycosidic torsion angle [C(6).sbd.N(1).sbd.C(1'').sbd.O(4'')] is 96.2(2).degree.. In the acyclic moiety, both C.sbd.OH bonds are guache with respect to C(4'').sbd.O(4''). The gauche conformation is also dominant in solution, as determined by high-resolution 1H nmr spectroscopy. Results of nuclear Overhauser experiments lead to conclusions about the flexibility of the molecule.

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