Studies on the Synthesis of 1-Deoxy-1-ureidoglucuronic Acid and Related Compounds. III

Synthesis of 1-(3-Arylthioureido)-1-deoxy-D-glucopyranuronic Acids or their Amides

Abstract

Reaction of aromatic amines with methyl 1-deoxy-1-isocyanato-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (I) affords methyl 1-(3-arylthioureido)-1-deoxy-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (II). Application of dilute alkali or methanolic amonia to (II) resulted in the formation of 1-(3-arylthioureido)-1-deoxy-β-D-glucopyranuronic acid (III) and -uronamide (IV) respectively. As part of these compounds, sulfamerazine and isonicotinic acid hydrazide derivatives were also prepared. Infrared spectra of these compounds exhibited absorption bands of thioureido group at 1550-1520cm^-1 and asymmetric stretching vibration of C-O-C in the β-pyranose ring at 1070cm^-1.