C-glycoside clustering on calix[4]arene, adamantane, and benzene scaffolds through 1,2,3-triazole linkers.
A route has been paved toward the preparation of triazole glycocluster libraries via the copper(I)-catalyzed modern version of the classical Huisgen 1,3-dipolar cycloaddition of azides to alkynes. Up to four 1,4-disubstituted 1,2,3-triazole rings bearing carbon-linked glycosyl fragments were constructed on various scaffolds via multiple cycloadditions of suitably polyfunctionalized calix[4]arene, adamantane, and benzene derivatives with ethynyl and azidomethyl C-glycosides. Each cycloaddition occurred with high regioselectivity to give exclusively the 1,4-disubstituted triazole ring in very high yield up to an average value of 98%. The high degree of efficiency of this approach and its wide scope constitute a simple and practical means for the attachment of various sugar units to polyfunctionalized substrates.
Dondoni
Alessandro
A
Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy. adn@dns.unife.it
Marra
Alberto
A
D000218:Adamantane / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D001554:Benzene / Q000737:chemistry*; D047250:Calixarenes / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003432:Cross-Linking Reagents; D006027:Glycosides; D009005:Monosaccharides / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry
D000480:Alkynes; D001386:Azides; C438934:C-glycoside; D003432:Cross-Linking Reagents; D006027:Glycosides; D009005:Monosaccharides; D010636:Phenols; D014230:Triazoles; C121325:calix(4)arene; D047250:Calixarenes; D001554:Benzene; D000218:Adamantane