Glycosyl fluorides from n-pentenyl-related glycosyl donors-application to glycosylation strategies
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 compl...
Published in: | Canadian Journal of Chemistry |
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Main Authors: | , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
National Research Council Canada
2013
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Subjects: | |
Online Access: | http://hdl.handle.net/10261/84465 https://doi.org/10.1139/cjc-2012-0285 |
Summary: | 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 |
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