A Synthesis of N-(2-Deoxy-β-D-glucopyranosyl)-N'-(4-aminomethyl-2-imino-1,3-thiazoline)urea Derivatives

Abstract

N-(2-Deoxy-β-D-glucopyranosyl)-N'-(4-aminomethyl-2-imino-1,3-thiazoline)urea derivatives 7 were synthesized from a reaction of isocyanato-β-D-glucopyranose 6 with 4-aminomethyl-2-phenylimino-1,3-thiazoline derivatives 4. β-D-glucopyranosyl isothiocyanate 6 was obtained by a dehydrochlorination of β-D-glucosamine hydrogenchloride salt 5 followed by the reaction of triphogene, which was unstable to isolate at room temperature. 4-Phthalimidyl-1,3-thiazoline dervitives derivatives 3 were prepared by a reaction of α-bromoketophthalimide 1 with the corresponding N-methyl-N'-phenylthioureas 2, of which phthalimidyl protecting group was deprotected by the treatment of methylamine to give the 4-aminomethyl-1,3-thiazolines 4. The effective methodology for synthesis of β-D-glucopyranose derivatives in which ureido function was introduced at C-2 was presented from this study.