IPy 2 BF 4 ‐Mediated Glycosylation and Glycosyl Fluoride Formation

• Published in: European Journal of Organic Chemistry
• Main Authors: Huang, Kuo‐Ting, Winssinger, Nicolas
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2007
• Subjects: Organic Chemistry; Physical and Theoretical Chemistry; IPY
• Online Access: http://dx.doi.org/10.1002/ejoc.200700038; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.200700038; https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.200700038

Abstract 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)