ChemInform Abstract: Reactions with and in Water‐Free Hydrogen Fluoride. Part 3. Selective Syntheses of Glycosyl Fluorides.

Abstract

254ChemInform Abstract Using the refluxing two-phase system Et3N•HF/CCl4 or the homogeneous system HF/MeNO2, the preparation of anomerically pure glycosyl fluorides such as (II) or (IV) is achieved avoiding the use of expensive AgF, the long reaction times of KHF2 and the laborious drying methods for water-soluble solvents such as MeCN.

Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century

“…This protocol also worked with hemiacetals ( vide infra ), and the yield could be enhanced with TiF 4 additive. Miethchen and co-workers also achieved bromine–fluorine exchange in the presence of two-phase system Et 3 N-3HF/CCl 4 . , This protocol also worked with hemiacetals as starting materials.…”

“…Miethchen and co-workers also achieved bromine−fluorine exchange in the presence of two-phase system Et 3 N-3HF/CCl 4 . 418,419 This protocol also worked with hemiacetals as starting materials.…”