SYNTHESIS OF SUGAR N-(2-THIAZOLIN-2-YL)THIOUREAS

Article abstract of DOI:10.1016/0008-6215(90)84296-7

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-isothiocyanato-α- or -β-D-glucopyranose (4 or 5) was condensed with 2-chloroethylamine hydrochloride in pyridine to afford N,N'-bis(1,2,3,4,6-tetra-O-acetyl-2-deoxy-α- or -β-D-glucopyranos-2-yl)-N-(2-thiazolin-2-yl)thiourea (2 or 3).When the reactions were carried out in ether, 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2-thiazolin-2-yl)amino-α- and -β-D-glucopyranose (6 and 7) were isolated and converted into the mixed N-(2-thiazolin-2-yl)-urea and thioureas (9-12) by reaction with iso(thio)cyanates.Bromine-promoted cyclisation of 1,3,4,6-tetra-O-acetyl-2-(N'-allylthioureido)-2-deoxy-α-D-glucopyranose (13) gave a mixture of the diastereomers 1,3,4,6-tetra-O-acetyl-2-<5(R and S)-5-bromomethyl-2-thiazolin-2-yl>amino-2-deoxy-α-D-glucopyranose hydrobromides (14 and 15), which was transformed into the analogous N-(2-thiazolin-2-yl)thioureas (16-18).