IPy2BF4-Mediated Transformation of n-Pentenyl Glycosides to Glycosyl Fluorides:  A New Pair of Semiorthogonal Glycosyl Donors

Bis(pyridinium) iodonium(I) tetrafluoroborate (IPy2BF4), a solid and stable reagent, can be used to transform n-pentenyl orthoesters (NPOEs) and n-pentenyl glycosides (NPGs) into glycosyl fluorides. The latter pair constitutes a new set of semiorthogonal glycosyl donors that can be used in glycosyla...

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Bibliographic Details
Published in:Organic letters 2007-07, Vol.9 (15), p.2759-2762
Main Authors: López, J. Cristóbal, Uriel, Clara, Guillamón-Martín, Alejandra, Valverde, Serafín, Gómez, Ana M
Format: Article
Language:English
Subjects:
Fluorides - chemistry
Glycosides - chemistry
Glycosylation
Onium Compounds - chemistry
Pyridines - chemistry
Online Access:Get full text
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Summary:Bis(pyridinium) iodonium(I) tetrafluoroborate (IPy2BF4), a solid and stable reagent, can be used to transform n-pentenyl orthoesters (NPOEs) and n-pentenyl glycosides (NPGs) into glycosyl fluorides. The latter pair constitutes a new set of semiorthogonal glycosyl donors that can be used in glycosylation strategies, alone or in combination with NPOEs.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol070753r