Method of preparation of 2-chloro-2-deoxysaccharides

Details Method of preparation of 2-chloro-2-deoxysaccharides Method of preparation of 2-chloro-2-deoxysaccharides

1979-10-17

1981-04-14

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536 1, 536 4, C07H 502

Patent

active

042621151

ABSTRACT:
A process for the preparation of a 2-chloro-2-deoxy-mono-, di- or oligo-saccharide comprises reaction of a mono-, di- or oligo-saccharide derivative having a free hydroxy group in at least 2- position and having the hydroxy group in at least the 1- and 3- positions protected from chlorination, with sulphuryl chloride in the presence of an organic base in a chlorinated hydrocarbon solvent at a temperature below -40.degree. C. to form a chlorosulphate derivative with a chlorosulphate group in at least the 2-position, which chlorosulphate derivative is then reacted with lithium chloride in the presence of hexamethylphosphoric triamide to replace chlorosulphate groups with chlorine atoms to form a chlorodeoxy derivative, which chlorodeoxy derivative is then freed of unwanted protecting groups.

REFERENCES:
patent: 4117224 (1978-09-01), Khon et al.
Chemical Abstracts, vol. 84, 31328b, 1976.
Chemical Abstracts, vol. 85, 2289e, 1976.
Chemical Abstracts, vol. 77, 85005t, 1972.

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