Abstract
AbstractIn 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 donor–spacer–acceptor‐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.
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