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First synthesis of 1,2,3-triazolo-linked (1,6)-alpha-D-oligomannoses (triazolomannoses) by iterative Cu(I)-catalyzed alkyne-azide cycloaddition
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First synthesis of 1,2,3-triazolo-linked (1,6)-alpha-D-oligomannoses (triazolomannoses) by iterative Cu(I)-catalyzed alkyne-azide cycloaddition

Pavel Cheshev, Alberto Marra et Alessandro Dondoni
Organic & biomolecular chemistry, Vol.4(17), pp.3225-3227
01/01/2006
PMID: 17036109

Résumé

Alkynes Azides Carbohydrate Conformation Catalysis Glycosides - chemical synthesis Glycosides - chemistry Mannose - chemistry Models, Molecular Oligosaccharides - chemical synthesis Oligosaccharides - chemistry Triazoles - chemistry
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.

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