60084-14-2Relevant articles and documents
Thiazole C-nucleosides. III. Synthesis of pyranose analogues of tiazofurin
Kovacs,Herczegh,Batta,Farkas
, p. 5539 - 5548 (1991)
A large-scale synthesis of 3,4,5-tro-O-acetyl-2,6-anhydro-L-mannono- and D-gulonothioamides (5, 6) has been achieved from the corresponding nitriles. The Hantsch reaction of (5) or (6) with ethyl bromopyruvate afforded the expected thiazoles (7, 8) only in a low yield along with furan derivatives (9-11), the formation of which is rationalized by an acid-catalysed rearrangement-elimination process. The same Hantzsch reaction in the presence of barium carbonate yielded hydroxythiazolines (16, 17). Attempted dehydration of (16) or (17) with trifluoroacetic anhydride or trifluoroacetic anhydride/pyridine resulted in the formation of pent-1'-enopyranosylthiazoles (18-20). Deprotected thioamides (24, 25) furnished with ethyl bromopyruvate thiazoles (27, 28). The obtained thiazole esters (7, 8, 18-20, 27, 28) were transformed into new tiazofurin analogues (12, 13, 21-23).
Synthesis of C glycosyl thiazoles
Fuertes,Garcia Lopez,Garcia Munoz,Stud
, p. 4074 - 4077 (2007/10/05)
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