Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates
[Display omitted] ► Xtalfluor-E and -M convert thio-, seleno-, and telluroglycosides to glycosyl fluorides. ► Reaction occurs readily without need for additional NBS. ► Sulfoxides are also converted to glycosyl fluorides. ► Mechanistic support delivery of fluoride from tetrafluoroborate counterion....
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Veröffentlicht in: | Carbohydrate research 2012-08, Vol.357, p.16-22 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | [Display omitted]
► Xtalfluor-E and -M convert thio-, seleno-, and telluroglycosides to glycosyl fluorides. ► Reaction occurs readily without need for additional NBS. ► Sulfoxides are also converted to glycosyl fluorides. ► Mechanistic support delivery of fluoride from tetrafluoroborate counterion.
Glycosyl fluorides can be synthesized from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using the aminodifluorosulfinium tetrafluoroborate reagents Xtalfluor-E and -M, with or without added N-bromosuccinimide. Mechanistic studies provide evidence that fluoride is delivered from the tetrafluoroborate counterion. |
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ISSN: | 0008-6215 1873-426X |
DOI: | 10.1016/j.carres.2012.04.016 |