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

• 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

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.