Process for the preparation of glycosyl fluorides protected on the oxygen

US4751291A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Joachim Thiem · Hamburg, DE
• Hans-Matthias Deger · Hofheim, DE
• Wolfram Fritsche-Lang · Bensheim, DE
• Matthias Kreuzer · Munster, DE

Key dates

• Filing date: Sep 12, 1986
• Grant date: Jun 14, 1988
• Expiry date: Sep 12, 2006

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H15/18
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Glycosyl halides which are O-acylated or O-alkylated at least in the 2-position are transhalogenated with alkali metal hydrogen difluorides in a polar-aprotic solvent and, if appropriate, the product is anomerized with the addition of less than the stoichiometric amounts of an inorganic fluoride with a Lewis acid character. Depending on the substrate, the glycosyl fluorides with the 1,2-trans or 1,2-cis configuration are obtained.