Glycosyl fluorides from n-pentenyl-related glycosyl donors-application to glycosylation strategies

• Published in: Canadian Journal of Chemistry
• Main Authors: Fraser-Reid, B., López, J. Cristóbal, Bernal-Albert, P., Gómez, Ana M., Uriel, Clara, Ventura, Jacint
• Format: Article in Journal/Newspaper
• Language: English
• Published: National Research Council Canada 2013
• Subjects: IPY
• Online Access: http://hdl.handle.net/10261/84465; https://doi.org/10.1139/cjc-2012-0285

n-Pentenyl glycosides (NPGs) and n-pentenyl orthoesters (NPOEs) have been transformed into glycosyl fluorides by a variety of methods. In the case of NPGs, Barluenga's reagent, bis(pyridinium)iodonium(I)tetrafluoroborate (IPy 2BF4), gives good yields of glycosyl fluorides when HF-pyridine complex is used as an additional fluoride source. NPOEs can be activated either by a combination of electrophilic iodonium (Barluenga's reagent) and HBF4 or by the action of HF-pyridine complex. The ensuing glycosyl fluorides form a semiorthogonal pair of glycosyl donors when confronted with NPGs. © 2012 Published by NRC Research Press. Peer Reviewed