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Abstract 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 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.
Tiwari et al. (Fri,) studied this question.