Stereocontrolled synthesis of imidazolo[1,5]hexopiperidinoses and imidazol-4(5)-yl-C-glycosides
2003; Elsevier BV; Volume: 59; Issue: 34 Linguagem: Inglês
10.1016/s0040-4020(03)01055-x
ISSN1464-5416
AutoresAndrzej Frankowski, Dariusz Deredas, Estelle Dubost, F. Gessier, Stefan Jankowski, Markus Neuburger, C. SELIGA, Théophile Tschamber, Kamil Weinberg,
Tópico(s)Synthesis of Indole Derivatives
ResumoThe syntheses of imidazolo[1,5]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.
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