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  • Synthesis of sugar N-(2-thiazolin-2-yl)thioureas
  • Add time:09/24/2019         Source:sciencedirect.com

    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(1,3,4,6-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).

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