Carbohydrate Research p. 247 - 258 (1990)
Update date:2022-07-29
Topics: Chemical shifts Isocyanate Pyridine Heterocyclic carbons Conformation J values Antiperiplanar arrangement Intramolecular hydrogen bond Acetone Isothiocyanate Purification and characterization Deprotection (if necessary) Protection of the Sugar Hydroxyl Groups Conversion to Sugar Isocyanate Preparation of Thiosemicarbazide Formation of N-(2-Thiazolin-2-yl)thioureas
Avalos, Martin
Rabiano, Reyes
Cintas, Pedro
Jimenez, Jose L.
Palacios, Juan C.
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).
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