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Stereocontrolled synthesis of imidazolo[1,5]hexopiperidinoses and imidazol-4(5)-yl-C-glycosides |
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| Authors: | Andrzej Frankowski Dariusz DeredasEstelle Dubost François GessierStefan Jankowski Markus NeuburgerCzes?awa Seliga Théophile TschamberKamil Weinberg |
| Institution: | a Institute of Organic Chemistry, Technical University of Lodz, ul. Zwirki 36, 90924 Lodz, Poland b Ecole Nationale Supérieure de Chimie, Université de Haute-Alsace, 3 rue Alfred Werner, 68093 Mulhouse, France c Institut für anorganische Chemie, Universität Basel, Spitalstrasse 51, CH-4056 Basel, Switzerland |
| Abstract: | The syntheses of imidazolo1,5]hexopiperidinoses 2-6 and imidazol-4(5)-yl C-glycosides 7-9 are reported. The crucial step of this approach relies upon the SN2-type cyclisation of selectively protected C(1), C(2), C(3) and C(5)-substituted 1-imidazol-4(5)-yl]pentitols in which the imidazole nitrogen or the C(1)-connected oxygen are involved as the competitive nucleophilic centers, respectively. Six selected imidazolosugars were evaluated as potential inhibitors of glycosidases. |
| Keywords: | imidazolohexapiperidinoses imidazolyl-C-glycosides glycosidase inhibition |
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