Preparation of sucrose 6,6'-dichloro hexa-acetate

Details Preparation of sucrose 6,6'-dichloro hexa-acetate Preparation of sucrose 6,6'-dichloro hexa-acetate

1975-12-11

1978-09-26

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536122, C07H 502

Patent

active

041172248

ABSTRACT:
6,6'-Dichloro-6,6'-dideoxysucrose is obtained directly in high yield by reacting sucrose with methanesulphonyl chloride in N,N-dimethylformamide. 1',6,6'-Trichloro-1',6,6'-trideoxysucrose is obtained as a by-product and its formation can be suppressed by starting the reaction at -40.degree. C to -15.degree. C. The dichlorodideoxy and trichloro-trideoxy compounds, which are useful as intermediates for preparing other sucrose derivates, are most conveniently isolated from the reaction mixture in the form of their hexa-acetate and penta-acetate respectively, which are then deacetylated to give the free compounds.

REFERENCES:
patent: 2013034 (1935-09-01), Cox et al.
patent: 2174541 (1939-10-01), Walthausen et al.
patent: 2562883 (1951-08-01), Barham
patent: 3280103 (1966-10-01), Sinclair
Evans et al. "Chem. Abst." vol. 68, 1968, p. 87497(t).
Evans et al. "The Jour. of Organic Chem." Mar. 1968, pp. 1074-1076.
Bolton et al. "Carbohydrate Research" 21, 1972 pp. 133-143.
Hough et al "Carbohydrate Research" 25, 1972 pp. 497-503.

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