Tate & Lyle Public Limited Company

Tate & Lyle, Inc.

Talres Development (n.a.) N.v.

Chemical Bank

Talres Development (n.a.)

Riaz A Khan

Michael R Jenner

Khizar S Mufti

Jonathan S Dordick

Andrew J Hacking

Leslie Hough

Shashikant P Phadnis

Kenneth John Parker

Haydn Frederick Jones

Graham Jackson

Peter S Cheetham

George H Sankey

Elner B Rathbone

Philip J Simpson

Nicholas M Vernon

Geoffrey M Waites

Jin Zhao

Andrew Pelter

Gita D Patel

Keith Smith

Khisar S Mufti

Alan C Richards

William C Ford

A method for the preparation of a sucrose 6-ester comprises:

Process for the preparation of sucrose 6-esters

Sucrose or derivatives thereof such as esters are acylated at the 4'- and/or the 6- position by reaction with a donor acyl ester, e.g. a reactive ester of an alkanoic acid or benzoic acid, in the presence of lipase. Sucrose 6,4' so produced can be chlorinated and deacylated to produce the sweetener sucralose.

Sucrose 6,4'-dicarboxylic esters

A process for the chlorination of sucrose or a derivative thereof, comprises reaction of the sucrose or derivative thereof with thionyl chloride and a nitrogen base at a ratio of about 1 molar equivalent (ME) of thionyl chloride and about 1 ME of base for every ME of free hydroxyl, in a non-reactive moderately polar solvent. The process is particularly suitable for the preparation of sucralose.

Chlorination of sugars

Sucrose or derivatives thereof such as esters are acylated at the 4'- and/or the 6-position by reaction with a donor acyl ester, e.g. a reactive ester of an alkanoic acid or benzoic acid, in the presence of lipase. Sucrose 6,4'-diesters so produced can be chlorinated and deacylated to produce the sweetener sucralose.

Selective acrylation of sugars

The novel chlorinated sugar O-.alpha.-D-6-chloro-6-deoxygalactopyranosyl-(1.fwdarw.6)-.alpha.-D-4-chlo ro-4-deoxygalactopyranosyl-(1.fwdarw.2)-.beta.-D-1, 6-dichloro-1, 6-dideoxyfructofuranoside (TCR) can be used to prepare sucralose by incubating the TCR in solution in the presence of an enzyme serving to remove the 6-chloro-6-deoxygalactosyl moiety from the 6-position, especially an enzyme derived from a strain of Mortierella vinacea, Circinella muscae or Aspergillus niger. TCR is prepared by treating raffinose with thionyl chloride in the presence of triphenylphosphine oxide.

Tetrachlororaffinose and its use in the preparation of sucralose

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.

Trichloro, 6-substituted sucrose compounds, compositions and uses

A method of sweetening a substance comprises incorporating therein a mono- or poly- chloro, mono- or poly- deoxy sucrose derivative having chlorine atoms in selected combinations of positions 4,6,1'- and 6'- of the sucrose molecule. The compounds are many times sweeter than sucrose and are formulated as ingestible products, such as foodstuffs and beverages; oral compositions, such as toothpaste and chewing gum; or sweetening compositions, such as tablets, for addition to beverages, etc.

Chloro-substituted sucrose compounds

Compounds of the general formula (I) are potent sweeteners, especially 4,1',6'-tribromo-4,1',6'-trideoxygalactosucrose: ##STR1## in which R' represents a chlorine or bromine atom;

Brominated sucrose derivatives, compositions and methods of use

Sweeteners

A process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose (TGS) comprising the steps of:

Process for the preparation of

A new chlorinated sucrose derivative, 2,6,1',6'-tetrachloro-2,6,1',6'-tetradeoxy-mannosucrose, is used as a bittering agent, e.g. to replace quinine sulphate, in ingestible compositions such as Indian tonic water, and in non-ingestible compositions.

Bittering agents

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.

Method of preparation of 2-chloro-2-deoxysaccharides

Resins for use in making resin-coated granules are made by preparing a novolak resin from a phenol and formaldehyde in the presence of lactose and/or galactose, using an acid catalyst. Melt-coating the resin with an amine curing agent on to particulate refractory material gives resin-coated granules which can be moulded to make foundry moulds. The lactose and/or galactose can replace part of the phenol conventionally employed in preparing novolak resins and avoids the need for plasticizers.

Novolak resins containing lactose and/or galactose

A male fertility-inhibiting composition in unit dosage form, contains as an active ingredient a 6-chlorodeoxy-saccharide containing a pyranose or furanose ring of the formula ##STR1## where A represents the remainder of the pyranose or furanose ring, and has the formula C.sub.4 H.sub.7 O.sub.4 X (where X represents a hydrogen atom or another pyranose or furanose ring) in association with a physiologically acceptable carrier or excipient. The saccharide preferably contains a pyranose ring or furanose ring of the formula ##STR2## Also a method of controlling fertility in men or male animals comprises administering thereto a 6-chlorodeoxy-saccharide as defined above.

Male fertility-inhibiting compositions of 6-chlorodeoxy-saccharides

A novel cyclic acetal derivative of sucrose, 4,6-O-isopropylidenesucrose, is prepared by treating sucrose with 2,2-dimethoxypropane in N,N-dimethylformamide, in the presence of p-toluenesulphonic acid, suitably at room temperature. The product is conveniently isolated in the form of its hexa-acetate or hexabenzoate, by treatment with acetic anhydride or benzoyl chloride, respectively, in pyridine. The resulting compounds are valuable as synthetic intermediates and in conformational investigations.

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Sonning, United Kingdom

Riaz A Khan