First synthesis of 1,2,3-triazolo-linked (1,6)-alpha-D-oligomannoses (triazolomannoses) by iterative Cu(I)-catalyzed alkyne-azide cycloaddition.
The iterative copper(I)-catalyzed cycloaddition (rt or microwave) between an ethynyl alpha-C-mannoside and alkyl 6-azido-alpha-C-mannoside derivatives was suited to the (1,6)-ligation between alpha-D-mannose units through 1,4-disubstituted triazole bridges, thus resulting in the formation of linear oligomers (80-90% yield) with alternating triazole and mannose fragments up to a triazolo-pentamannose derivative.
Cheshev
Pavel
P
Laboratorio di Chimica Organica, Dipartimento di Chimica, Via Borsari 46, 44100 Ferrara, Italy.
Marra
Alberto
A
Dondoni
Alessandro
A
D000480:Alkynes; D001386:Azides; D002236:Carbohydrate Conformation; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry; D008358:Mannose / Q000737:chemistry*; D008958:Models, Molecular; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry
D000480:Alkynes; D001386:Azides; D006027:Glycosides; D009844:Oligosaccharides; D014230:Triazoles; C028569:oligomannoside; D008358:Mannose