Collect. Czech. Chem. Commun. 1979, 44, 1339-1342

Synthesis of 5-β-D-ribofuranosyl-1,3-thiazole-2-carboxamide - A thiazole analogue of ribavirin

Tomáš Vaněk, Jiří Farkaš and Jiří Gut

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Condensation of ethyl thioxamate (II) with bromomethyl D-ribo-1,2,3,4-tetraacetoxybutyl ketone (I) or bromomethyl 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl ketone (IX) afforded ethyl 5-(D-ribo-1,2,3,4-tetraacetoxybutyl)-1,3-thiazole-2-carboxylate (III) and ethyl 5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3-thiazole-2-carboxylate (X), respectively. Removal of the protecting groups and ammonolysis of the ester gave the respective 5-(D-ribo-1,2,3,4-tetrahydroxybutyl)-1,3-thiazole-2-carboxamide (V) and 5-(β-D-ribofuranosyl)-1,3-thiazole-2-carboxamide (XI).