IPy2BF4/HF-pyridine: a new combination of reagents for the transformation of partially unprotected thioglycosides and n-pentenyl glycosides to glycosyl fluorides

J Org Chem. 2007 Dec 21;72(26):10268-71. doi: 10.1021/jo7018653. Epub 2007 Nov 29.

Abstract

The combination of bis(pyridinium)iodonium (I) tetrafluoroborate (IPy2BF4), and hydrogen fluoride pyridine (HF-py) forms an iodine monofluoride (IF) synthetic equivalent that can be used in the preparation of partially unprotected glycosyl fluorides from partially unprotected n-pentenyl glycosides and thioglycosides, thus avoiding the need for the protection/deprotection steps normally required in that transformation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Fluorides / chemistry*
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry*
  • Halogenation
  • Hydrofluoric Acid / chemistry*
  • Onium Compounds / chemistry*
  • Pyridines / chemistry*
  • Stereoisomerism

Substances

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