Preparation and properties of 2-deoxyglycosyl isothiocyanates

Article abstract of DOI:10.1016/S0040-4020(01)86530-3

The syntheses of 3,4,6-tri-O-acetyl-2-deoxy-α and β-D-arabino(D-lyxo)hexopyranosyl isothiocyanates (2, 3, 6, 7) and 4, 6-di-O-acetyl-3-bromo-2,3-dideoxy-β-D-arabinohexopyranosyl isothiocyanate (5) are reported. Treatments of 2,3,6, and 7 with phenacylamine hydrochloride and of 2 with aminoacetone hydrochloride gave the corresponding N-phenacyl (acetylmethyl-N'-(2-deoxyglycosyl)-thioureas (8-12). The N-nucleoside analogues 5-methyl-1-(3',4',6'-tri-O-acetyl-2'-deoxy-α-D- arabinohexopyranosyl)-4-imidazoline-2-thione (13) was obtained by cyclodehydration of the thiourea 12.