The Syntheses of Glycosylbarbiturate.

Abstract
By condensation of 1-(2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranosyl) urea (IV) with malonyl chloride in pyridine, N, N'-bis (2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranosylcarbamoyl)-malondiamide (V) was obtained. This compound, when treated with alkali, afforded each one mole of 1-(β-D-glucopyranosyl) urea and sodium 1-(β-D-glucopyranosyl) barbiturate (VI). Condensation of 1-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl) urea (VII) with malonic acid in acetic anhydride gave N, N'-bis (2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl-carbamoyl) malondiamide (VIII) with a small amount of 1-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl)-5-acetylbarbituric acid (IX). On alkaline treatment, VIII afforded sodium 1-(β-D-ribofuranosyl) barbiturate (X) and 1-(β-D-ribofuranosyl) urea (XI). The overall yield of VI and X from IV and VII were 30.3% and 37% respectively. The stucture of the glycosylbarbiturates, VI and X, were discussed and their properties were described.