EP0010410A2
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EP
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A method for the preparation of 2-chloro-2-deoxy saccharides and some 2-chloro-2-deoxy saccharides
Assignee: Tate & Lyle Patent Holdings Ltd
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Filing: 1979-10-12
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Granted: —
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Expires: 1999-10-12
Abstract
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-sap q haride 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°C to form a chlorosulphate derivative with a chlorosulphate derivative isthen 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.
Inventors
- 👤 Riaz Ahmed Khan
- 👤 Michael Ralph Jenner
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-01 02:41
CPC Classifications
C; C07; C07H; C07H5/00; C07H5/02; A; A01; A01N; A01N43/00; A01N43/02; A01N43/04; A01N43/14; A01N43/16; A23; A23K; A23K20/00; A23K20/10; A23K20/163; A23L; A23L27/00; A23L27/20; A23L27/205; A23L27/2052; A23L27/30; A23L27/33; A23L27/37; C07H13/00; C07H13/02; C07H13/04; C07H13/08; C07H15/00; C07H15/02; C07H15/04; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
120 words
A process for the preparation of a chlorodeoxy saccharide by reaction of a saccharide derivative with sulphuryl chloride followed by reaction with lithium chloride, and removal of unwanted protecting groups, characterised in that 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, is reacted with sulphuryl chloride in the presence of an organic base in a chlorinated hydrocarbon solvent at a temperature below -40 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 a polar aprotic solvent.
Claim 2
Dependent Claim
120 words
A process for the preparation of a chlorodeoxy saccharide by reaction of a saccharide derivative with sulphuryl chloride followed by reaction with lithium chloride, and removal of unwanted protecting groups, characterised in that 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, is reacted with sulphuryl chloride in the presence of an organic base in a chlorinated hydrocarbon solvent at a temperature below -40 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 a polar aprotic solvent.
Claim 3
Dependent Claim
15 words
A process according to claim 1, in which the organic base is a tertiary amine.
Claim 4
Dependent Claim
13 words
A process according to claim 1, in which the chlorinated hydrocarbon is chloroform.
Claim 5
Dependent Claim
22 words
A process according to claim 3, in which chloroform and pyridine are used in a volume ratio of 2. 5:1 to 3.5:1.
Claim 6
Dependent Claim
19 words
A process according to claim 1, in which the temperature of reaction with sulphuryl chloride is about -70 C.
Claim 7
Dependent Claim
14 words
A process according to claim 1, in which the aprotic solvent is hexamethylphosphoric triamide.
Claim 8
Dependent Claim
23 words
A process according to claim 1, in which the reaction with lithium chloride is effected at a temperature of from 40° to 100°C.
Claim 9
Dependent Claim
27 words
A compound of the general formula Where X represents a hydrogen atom and R' represents a hydroxy group; or X represents an aglycone of the general formula
Claim 10
Dependent Claim
27 words
A compound of the general formula Where X represents a hydrogen atom and R' represents a hydroxy group; or X represents an aglycone of the general formula
Claim 11
Dependent Claim
25 words
A compound according to claim 8, selected from the group consisting of 2, 1'-dichloro-2,1'-dideoxymannosucrose, 2-chloro-2-deoxymannosucrose, 2-chloro-2-deoxymannose, and 2, 1', 6, 6'-Tetrachloro-2, 1', 6, 6' -tetradeoxymannosucrose.
References Cited (Backward Citations)
No citation records indexed.
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