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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)