Chlorination of carbohydrates and other alcohols

C - Chemistry – Metallurgy – 07 – H

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C07H 5/02 (2006.01) C07B 39/00 (2006.01) C07C 17/16 (2006.01) C07D 493/04 (2006.01) C07H 13/04 (2006.01)

Patent

CA 1284495

ABSTRACT OF THE DISCLOSURE There is a known process for the preparation of 1,6-dichloro-1,6-dideoxy-.beta.-D-fructofuranosyl-4- chloro-4-deoxy-a-galactopyranoside by reacting sucrose with a tritylating agent, acetylating the tritylated reaction product with an acetylating agent to obtain 6,1',6'-tri-O-tritylsucrose penta-acetate, detritylating the 6,1',6'-tri-O-tritylsucrose penta-acetate to obtain 2,3,4,3',4'-penta-O-acetylsucrose, isomerizing the 2,3,4,3',4'-penta-O-acetylsucrose to obtain 2,3,6,3',4'-penta-O-acetylsucrose, chlorinating the latter product with a chlorinating agent to obtain 4,1',6'-trichloro-4,1',6.-trideoxygalactosucrose penta- acetate, and deacetylating the chlorinating product. According to the invention, the chlorinating step utilises a chlorinating agent selected from the group consisting of triphenylphosphine oxide/thionyl chloride, triphenylphosphine oxide/phosgene, triphenylphosphine sulfide/thionyl chloride and triphenylphosphine sulfide/phosgene in the presence of an aromatic hydro- carbon solvent at a temperature up to about 120°C. This chlorinating agent is efficient and eliminates the use of a pyridine as a solvent.

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