Disaccharide-Containing Macrocycles by Click Chemistry and Intramolecular Glycosylation

作者：Tiwari Vinod K; Kumar Amit; Schmidt Richard R^*

来源：European Journal of Organic Chemistry, 2012, (15): 2945-2956.

DOI：10.1002/ejoc.201101815

• Carbohydrates
• Glycosylation
• Macrocycles
• Nitrogen heterocycles
• Click chemistry

In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyranoside was employed as a donor, which could be readily connected by 1,3-dipolar cycloaddition (click reaction) to O-(2- or 3-azidomethylbenzyl)-protected acceptors to afford, after liberation of the accepting hydroxy groups, the desired donorspaceracceptor-linked intermediates. NIS/TMSOTf-promoted glycosylation furnished disaccharide-containing macrocycles. In general, very good results were obtained. The anomeric selectivity is dependent on various factors, the ring size seeming crucial.

• 出版日期2012-5