Synthesis of imidazo[2,1-b]thiazoles linked to an unprotected carbohydrate moiety

Two series of imidazo[2,1-b]thiazoles substituted on C-3 or C-5 with an unprotected carbohydrate moiety were synthesized. Different protective groups for position 3 of the carbohydrate moiety were tested (acetyl, tert-butyldimethylsilyl (TBDMS), and p-methoxybenzyl (PMB)) and the latter turn out to be the best strategy to obtain the desired products. Full deprotection of the carbohydrate was performed successfully in only one step.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Synthesis of imidazo[2,1-b]thiazoles linked to an unprotected carbohydrate moiety. ► A convenient protective group for position 3 of a carbohydrate. ► Microwave assistance of N-alkylation step.