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Título: | Glycosyl fluorides from n-pentenyl-related glycosyl donors-application to glycosylation strategies |
Autor: | Fraser-Reid, B.; López, J. Cristóbal; Bernal-Albert, Paloma CSIC; Gómez, Ana M. CSIC ORCID ; Uriel, Clara CSIC ORCID; Ventura, Jacint | Fecha de publicación: | 2013 | Editor: | National Research Council Canada | Citación: | Canadian Journal of Chemistry 91: 51- 65 (2013) | Resumen: | 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. | URI: | http://hdl.handle.net/10261/84465 | DOI: | 10.1139/cjc-2012-0285 | Identificadores: | doi: 10.1139/cjc-2012-0285 issn: 0008-4042 e-issn: 1480-3291 |
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