Process for the preparation of glycosyl fluorides protected on t

Details Process for the preparation of glycosyl fluorides protected on t Process for the preparation of glycosyl fluorides protected on t

1986-09-12

1988-06-14

Griffin, Ronald W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 184, C07H 502, C07H 1300, C07H 1500

Patent

active

047512911

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.

REFERENCES:
patent: 4659810 (1987-04-01), Thiem et al.
A. A. E. Penglis (Adv. Carbohydr. Chem. Biochem., 38, 195-285 (1981).
A. B. Foster and J. H. Westwood (Pure Appl. Chem., 35, 147-168 (1973).
A. Bertho (Ber. Dtsch. Chem. Ges., 63, 836 (1930)).
Chemical Abstracts, 73, (1970), 35645y.
Carbohydrate Research, 132, (1984), pp. 339-341.
Chemical Abstracts, 80, (1974), 96243q.
Chemical Abstracts, 95, (1981), 43491q.

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