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Disaccharide‐Containing Macrocycles by Click Chemistry and Intramolecular Glycosylation
Author(s) -
Tiwari Vinod K.,
Kumar Amit,
Schmidt Richard R.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101815
Subject(s) - chemistry , disaccharide , intramolecular force , moiety , glycosylation , click chemistry , cycloaddition , stereochemistry , anomer , propargyl , 1,3 dipolar cycloaddition , acceptor , combinatorial chemistry , organic chemistry , catalysis , biochemistry , condensed matter physics , physics
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.