IPy 2 BF 4 ‐Mediated Glycosylation and Glycosyl Fluoride Formation | Zendy

Huang KuoTing | Zendy; Winssinger Nicolas | Zendy

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IPy 2 BF 4 ‐Mediated Glycosylation and Glycosyl Fluoride Formation

Author(s) -

Huang KuoTing,

Winssinger Nicolas

Publication year - 2007

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200700038

Subject(s) - chemistry , glycosyl , glycosylation , anomer , fluoride , pyridine , glycosyl donor , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , inorganic chemistry

A facile method to convert thioglycosides to glycosyl fluorides with Ipy 2 BF 4 (py = pyridine) is presented. Alternatively, activation of thioglycosides with Ipy 2 BF 4 in the presence of acids and glycosyl acceptors led to glycosylation reactions. Perbenzylated (armed) glycosyl donors yielded predominantly the β‐anomeric product. This methodology is compatible with one‐pot sequential glycosylation.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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