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

AnHsiang Adam Chu | Zendy; Andrei Minciunescu | Zendy; Vittorio Montanari | Zendy; Krishna Kumar | Zendy; Clay S. Bennett | Zendy

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

Author(s) -

AnHsiang Adam Chu,

Andrei Minciunescu,

Vittorio Montanari,

Krishna Kumar,

Clay S. Bennett

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol5004059

Subject(s) - chemistry , glycosidic bond , salt (chemistry) , yield (engineering) , glycosylation , combinatorial chemistry , moisture , simplicity , glycan , organic chemistry , biochemistry , glycoprotein , philosophy , epistemology , materials science , metallurgy , enzyme

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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