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

AuthorsFraser-Reid, B.; López, J. Cristobal; Bernal-Albert, P.; Gómez, Ana M. ; Uriel, Clara ; Ventura, Jacint
Issue Date2013
PublisherNational Research Council Canada
CitationCanadian Journal of Chemistry 91: 51- 65 (2013)
Abstractn-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.
Identifiersdoi: 10.1139/cjc-2012-0285
issn: 0008-4042
e-issn: 1480-3291
Appears in Collections:(IQOG) Artículos
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