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 2 BF 4 ), gives good yields of glycosyl fluorides when HF–pyridine complex...

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Bibliographic Details
Published in:Canadian Journal of Chemistry
Main Authors: Fraser-Reid, Bert, Lopez, J. Cristobal, Bernal-Albert, Paloma, Gomez, Ana M., Uriel, Clara, Ventura, Juan
Format: Article in Journal/Newspaper
Language:English
Published: Canadian Science Publishing 2013
Subjects:
Organic Chemistry
General Chemistry
Catalysis
IPY
Online Access:http://dx.doi.org/10.1139/cjc-2012-0285
http://www.nrcresearchpress.com/doi/full-xml/10.1139/cjc-2012-0285
http://www.nrcresearchpress.com/doi/pdf/10.1139/cjc-2012-0285
Description
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 2 BF 4 ), 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 HBF 4 or by the action of HF–pyridine complex. The ensuing glycosyl fluorides form a semiorthogonal pair of glycosyl donors when confronted with NPGs.

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