Publikation: Disaccharide-Containing Macrocycles by Click Chemistry and Intramolecular Glycosylation
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2012
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European Journal of Organic Chemistry. 2012, 2012(15), pp. 2945-2956. ISSN 1434-193X. eISSN 1099-0690. Available under: doi: 10.1002/ejoc.201101815
Zusammenfassung
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.
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540 Chemie
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Carbohydrates, Glycosylation, Macrocycles, Nitrogen heterocycles, Click chemistry
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TIWARI, Vinod K., Amit KUMAR, Richard R. SCHMIDT, 2012. Disaccharide-Containing Macrocycles by Click Chemistry and Intramolecular Glycosylation. In: European Journal of Organic Chemistry. 2012, 2012(15), pp. 2945-2956. ISSN 1434-193X. eISSN 1099-0690. Available under: doi: 10.1002/ejoc.201101815BibTex
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year={2012},
doi={10.1002/ejoc.201101815},
title={Disaccharide-Containing Macrocycles by Click Chemistry and Intramolecular Glycosylation},
number={15},
volume={2012},
issn={1434-193X},
journal={European Journal of Organic Chemistry},
pages={2945--2956},
author={Tiwari, Vinod K. and Kumar, Amit and Schmidt, Richard R.}
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