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Org Lett. 2014 Mar 21;16(6):1780-2. doi: 10.1021/ol5004059. Epub 2014 Mar 5.

An air- and water-stable iodonium salt promoter for facile thioglycoside activation.

Author information

1
Department of Chemistry, Tufts University , 62 Talbot Avenue, Medford, Massachusetts 02155, United States.

Abstract

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.

PMID:
24597905
PMCID:
PMC3993783
DOI:
10.1021/ol5004059
[Indexed for MEDLINE]
Free PMC Article

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