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US4262115A
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Method of preparation of 2-chloro-2-deoxysaccharides
Assignee: Tate and Lyle PLC
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Filing: 1979-10-17
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Granted: 1981-04-14
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Expires: 1999-10-17
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-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° 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.
Inventors
- 👤 Riaz A. Khan
- 👤 Michael R. Jenner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 14:28
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: 21
Claim 1
Independent Claim
120 words
A process for the preparation of a 2-chloro-2-deoxy-mono-, di- or oligo-saccharide, in which a mono-, di-, or oligo-saccharide derivative having a free hydroxy group in at least the 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 to replace chlorosulphate groups with chlorine atoms to form a chlorodeoxy derivative, which chlorodeoxy derivative is then freed of unwanted protecting groups.
Claim 2
Dependent Claim
120 words
A process for the preparation of a 2-chloro-2-deoxy-mono-, di- or oligo-saccharide, in which a mono-, di-, or oligo-saccharide derivative having a free hydroxy group in at least the 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 to replace chlorosulphate groups with chlorine atoms to form a chlorodeoxy derivative, which chlorodeoxy derivative is then freed of unwanted protecting groups.
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
14 words
A process according to claim 2, in which the base is a pyridine compound.
Claim 5
Dependent Claim
13 words
A process according to claim 1, in which the chlorinated hydrocarbon is chloroform.
Claim 6
Dependent Claim
21 words
A process according to claim 4, in which chloroform and pyridine are used in a volume ratio of 2.5:1 to 3.5:1.
Claim 7
Dependent Claim
19 words
A process according to claim 1, in which the temperature of reaction with sulphuryl chloride is about -70° C.
Claim 8
Dependent Claim
14 words
A process according to claim 1, in which the aprotic solvent is hexamethylphosphoric triamide.
Claim 9
Dependent Claim
24 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 10
Dependent Claim
14 words
A process according to claim 8, in which the temperature is about 70° C.
Claim 11
Dependent Claim
29 words
A process according to claim 1, in which the saccharide starting material has hydroxy groups protected by ester or ether groups or has hydroxy groups substituted by chlorine atoms.
Claim 12
Dependent Claim
26 words
A process according to claim 1, in which the saccharide starting material comprises at least one pentose or hexose ring in the pyranose or furanose form.
Claim 13
Dependent Claim
19 words
A process according to claim 11 in which the saccharide starting material is a glucose, sucrose or raffinose derivative.
Claim 14
Dependent Claim
35 words
A compound of the general formula ##STR3## where X represents an aglycone of the general formula ##STR4## where R 2 is chlorine and R 3 is the same as R' and is chlorine or hydroxy.
Claim 15
Dependent Claim
35 words
A compound of the general formula ##STR3## where X represents an aglycone of the general formula ##STR4## where R 2 is chlorine and R 3 is the same as R' and is chlorine or hydroxy.
Claim 16
Dependent Claim
1 words
2,1'-Dichloro-2,1'-dideoxymannosucrose.
Claim 17
Dependent Claim
1 words
2,1'-Dichloro-2,1'-dideoxymannosucrose.
Claim 18
Dependent Claim
1 words
2-Chloro-2-deoxymannosucrose.
Claim 19
Dependent Claim
1 words
2-Chloro-2-deoxymannosucrose.
Claim 20
Dependent Claim
1 words
2,1',6,6'-Tetrachloro-2,1',6,6'-tetradeoxymannosucrose.
Claim 21
Dependent Claim
1 words
2,1',6,6'-Tetrachloro-2,1',6,6'-tetradeoxymannosucrose.
References Cited (Backward Citations)
US4117224A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-04-13 | 1984-10-13 | 1985-04-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-13 | 1988-10-13 | 1989-04-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-13 | 1992-10-13 | 1993-04-14 | $7700.00 | Window Closed / Lapsed |