An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation

[Image: see text] The air- and water-stable iodonium salt phenyl(trifluoroethyl)iodonium triflimide is shown to activate thioglycosides for glycosylation at room temperature. Both armed and disarmed thioglycosides rapidly undergo glycosylation in 68–97% yield. The reaction conditions are mild and do...

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Autores principales: Chu, An-Hsiang Adam, Minciunescu, Andrei, Montanari, Vittorio, Kumar, Krishna, Bennett, Clay S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3993783/
https://www.ncbi.nlm.nih.gov/pubmed/24597905
http://dx.doi.org/10.1021/ol5004059
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author Chu, An-Hsiang Adam
Minciunescu, Andrei
Montanari, Vittorio
Kumar, Krishna
Bennett, Clay S.
author_facet Chu, An-Hsiang Adam
Minciunescu, Andrei
Montanari, Vittorio
Kumar, Krishna
Bennett, Clay S.
author_sort Chu, An-Hsiang Adam
collection PubMed
description [Image: see text] The air- and water-stable iodonium salt phenyl(trifluoroethyl)iodonium triflimide is shown to activate thioglycosides for glycosylation at room temperature. Both armed and disarmed thioglycosides rapidly undergo glycosylation in 68–97% yield. The reaction conditions are mild and do not require strict exclusion of air and moisture. The operational simplicity of the method should allow experimentalists with a limited synthetic background to construct glycosidic linkages.
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spelling pubmed-39937832015-03-05 An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation Chu, An-Hsiang Adam Minciunescu, Andrei Montanari, Vittorio Kumar, Krishna Bennett, Clay S. Org Lett [Image: see text] The air- and water-stable iodonium salt phenyl(trifluoroethyl)iodonium triflimide is shown to activate thioglycosides for glycosylation at room temperature. Both armed and disarmed thioglycosides rapidly undergo glycosylation in 68–97% yield. The reaction conditions are mild and do not require strict exclusion of air and moisture. The operational simplicity of the method should allow experimentalists with a limited synthetic background to construct glycosidic linkages. American Chemical Society 2014-03-05 2014-03-21 /pmc/articles/PMC3993783/ /pubmed/24597905 http://dx.doi.org/10.1021/ol5004059 Text en Copyright © 2014 American Chemical Society
spellingShingle Chu, An-Hsiang Adam
Minciunescu, Andrei
Montanari, Vittorio
Kumar, Krishna
Bennett, Clay S.
An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation
title An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation
title_full An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation
title_fullStr An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation
title_full_unstemmed An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation
title_short An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation
title_sort air- and water-stable iodonium salt promoter for facile thioglycoside activation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3993783/
https://www.ncbi.nlm.nih.gov/pubmed/24597905
http://dx.doi.org/10.1021/ol5004059
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