IPy2BF4-mediated transformation of n-pentenyl glycosides to glycosyl fluorides: a new pair of semiorthogonal glycosyl donors

Org Lett. 2007 Jul 19;9(15):2759-62. doi: 10.1021/ol070753r. Epub 2007 Jun 20.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fluorides / chemistry*
  • Glycosides / chemistry*
  • Glycosylation
  • Onium Compounds / chemistry*
  • Pyridines / chemistry*

Substances

  • Glycosides
  • Onium Compounds
  • Pyridines
  • bis(pyridine)iodonium(I) tetrafluoroborate
  • Fluorides