Abstract: A method for the preparation of a sucrose 6-ester comprises:(i) reacting sucrose with a ketene acetal in the presence of an acid catalyst in an inert organic solvent to form a sucrose alkyl 4, 6-orthoester;(ii) subjecting the sucrose alkyl 4, 6-orthoester to mild acidic hydrolysis to provide a mixture of 4- and 6-monoesters of sucrose; and(iii) treating the mixture of sucrose monoesters with a base to convert the sucrose 4-ester into sucrose 6-ester. Sucralose may be prepared by chlorination of sucrose 6-esters prepared according to the invention.
Type:
Grant
Filed:
May 21, 1992
Date of Patent:
August 8, 1995
Assignee:
Tate & Lyle Public Limited Co.
Inventors:
Riaz A. Khan, Keith Smith, Andrew Pelter, Jin Zhao
Abstract: Compounds of the general formula: ##STR1## (in which X represents a hydrogen atom or an alkoxy or arylalkoxy group) are new compounds; those where X represents a hydrogen atom or a methoxy group are potent sweeteners while those with a cleavable 6-ether group are key intermediates in the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose (TGS). They are prepared by chlorinating a sucrose 6-ether, by etherifying a suitably protected derivative of TGS or, in the case where X represents hydrogen, by debromination of 6-bromo-4,1',6'-trichloro-4,6,1',6'-tetradeoxygalactosucrose.
Type:
Grant
Filed:
September 12, 1983
Date of Patent:
September 16, 1986
Assignee:
Tate & Lyle Public Limited Co.
Inventors:
Riaz A. Khan, Khisar S. Mufti, Gita D. Patel