- Synthesis of Tiazofurin
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Tiazofurin (CAS NO.: ), with its systematic name of 4-Thiazolecarboxamide, 2-beta-D-ribofuranosyl-, could be produced through many synthetic methods.
Following is one of the reaction routes:
1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (I) could react with and SnCl4 in the preence of dichloromethane to produce 2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl cyanide (II), which is treated with H2S gas and dimethylaminopyridine (P) in ethanol yielding the corresponding thioamide (III). The carefully controlled cyclization of (III) with 3-bromo ethyl ester (IV) by means of NaHCO3 in dimethoxyethane, followed by treatment with trifluoroacetic anhydride and 2,6-lutidine in the same solvent affords 2-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)thiazole-4-carboxylic acid ethyl ester (V). Elimination of the benzoyl protecting groups of (V) with NaOEt in ethanol gives 2-(beta-D-ribofuranosyl)thiazole-4-carboxylic acid ethyl ester (VI). Which is finally treated with dry ammonia in methanol to afford the target amide.
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