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

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.

SUBMITTER: Chu AH

PROVIDER: S-EPMC3993783 | biostudies-other | 2014 Mar

REPOSITORIES: biostudies-other

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

Chu An-Hsiang Adam AH Minciunescu Andrei A Montanari Vittorio V Kumar Krishna K Bennett Clay S CS

Organic letters 20140305 6

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. ...[more]

PMID: 24597905

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