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US4117224A
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Preparation of sucrose 6,6'-dichloro hexa-acetate
Assignee: Tate and Lyle PLC
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Filing: 1975-12-11
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Granted: 1978-09-26
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Expires: 1995-12-11
Abstract
Abstract 6,6'-Dichloro-6,6'-dideoxysucrose is obtained directly in high yield by reacting sucrose with methanesulphonyl chloride in N,N-dimethylformamide. 1',6,6'-Trichloro-1',6,6'-trideoxysucrose is obtained as a by-product and its formation can be suppressed by starting the reaction at -40° C to -15° C. The dichlorodideoxy and trichloro-trideoxy compounds, which are useful as intermediates for preparing other sucrose derivates, are most conveniently isolated from the reaction mixture in the form of their hexa-acetate and penta-acetate respectively, which are then deacetylated to give the free compounds.
Inventors
- 👤 Riaz Ahmed Khan
- 👤 Khizar Sultan Mufti
- 👤 Kenneth John Parker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 21:37
CPC Classifications
C; C07; C07H; C07H5/00; C07H5/02; C07H13/00; C07H13/02; C07H13/04
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
45 words
A process for preparing a sucrose derivative, which comprises reacting a cooled solution of sucrose in N,N-dimethylformamide with methanesulphonyl chloride, contacting the resulting product in situ with an acetylating agent whereby the hexa-acetate of 6,6'-dichloro-6,6'-dideoxysucrose is formed, and isolating said hexa-acetate from the reaction mixture.
Claim 2
Dependent Claim
45 words
A process for preparing a sucrose derivative, which comprises reacting a cooled solution of sucrose in N,N-dimethylformamide with methanesulphonyl chloride, contacting the resulting product in situ with an acetylating agent whereby the hexa-acetate of 6,6'-dichloro-6,6'-dideoxysucrose is formed, and isolating said hexa-acetate from the reaction mixture.
Claim 3
Dependent Claim
53 words
The process according to claim 1, wherein the methanesulphonyl chloride is added to a solution of the sucrose in N,N-dimethylformamide at a temperature of from about -40° C. to about -15° C., and the resulting reaction mixture is then heated to a temperature of about 60°-70° C. in order to complete the reaction.
Claim 4
Dependent Claim
19 words
The process according to claim 1, wherein about 10 moles of methanesulphonyl chloride are used per mole of sucrose.
Claim 5
Dependent Claim
21 words
The process according to claim 1 wherein said hexa-acetate is deacetylated by contact with a deacetylating agent to give free 6,6'-dichloro-6,6'-dideoxysucrose.
Claim 6
Dependent Claim
52 words
A process for producing sucrose derivatives, which comprises reacting a cooled solution of sucrose in N,N-dimethylformamide with methanesulphonyl chloride, contacting the resulting product in situ with an acetylating agent whereby the hexa-acetate of 6,6'-dichloro-6,6'-dideoxysucrose and the penta-acetate of 1',6,6'-trichloro-1',6,6'-trideoxysucrose are formed, and isolating the hexa-acetate and penta-acetate from the the reaction mixture.
Claim 7
Dependent Claim
52 words
A process for producing sucrose derivatives, which comprises reacting a cooled solution of sucrose in N,N-dimethylformamide with methanesulphonyl chloride, contacting the resulting product in situ with an acetylating agent whereby the hexa-acetate of 6,6'-dichloro-6,6'-dideoxysucrose and the penta-acetate of 1',6,6'-trichloro-1',6,6'-trideoxysucrose are formed, and isolating the hexa-acetate and penta-acetate from the the reaction mixture.
Claim 8
Dependent Claim
19 words
The process according to claim 5, wherein about 10 moles of methanesulphonyl chloride are used per mole of sucrose.
Claim 9
Dependent Claim
27 words
The process according to claim 5 wherein said hexa-acetate and said penta-acetate are deacetylated by contact with a deacetylating agent to give free 6,6'-dichloro-6,6'-dideoxysucrose and 1',6,6'-trichloro-1',6,6'-trideoxysucrose, respectively.
Claim 10
Dependent Claim
22 words
The process according to claim 7, wherein the said hexa-acetate and penta-acetate are separated from each other by means of column chromatography.
Claim 11
Dependent Claim
35 words
The process according to claim 2 wherein about 10 moles of methanesulphonyl chloride are used per mole of sucrose, and wherein said hexa-acetate is deacetylated by contact with a deacetylating agent to give free 6,6'-dichloro-6,6'-dideoxysucrose.
Claim 12
Dependent Claim
51 words
The process according to claim 6 wherein the methanesulphonyl chloride is added to the solution of the sucrose at a temperature from about -40° C. to about -15° C., and the resulting mixture is then heated to a temperature of about 60° to 70° C. in order to complete the reaction.
Claim 13
Dependent Claim
26 words
The process according to claiam 10 wherein said hexa-acetate and penta-acetate are deacetylated by contact with a deacetylating agent to give free 6,6'-dichloro-6,6'-dideoxysucrose and 1',6,6'-trichloro-1',6,6'-trideoxysucrose, respectively.
Claim 14
Dependent Claim
26 words
The process according to claiam 10 wherein said hexa-acetate and penta-acetate are deacetylated by contact with a deacetylating agent to give free 6,6'-dichloro-6,6'-dideoxysucrose and 1',6,6'-trichloro-1',6,6'-trideoxysucrose, respectively.
Claim 15
Dependent Claim
35 words
The process according to claim 4 wherein said deacetylated free 6,6'-dichloro-6,6'-dideoxysucrose is re-acetylated by contact with an acetylating agent and the re-acetylated product is deacetylated by contact with a deacetylating agent to give free 6,6'-dichloro-6,6'-dideoxysucrose.
Claim 16
Dependent Claim
39 words
The process according to claim 7 wherein said deacetylated free 6,6'-dichloro-6,6'-dideoxysucrose and 1',6,6'-trichloro-1',6,6'-trideoxysucrose is re-acetylated by contact with an acetylating agent and the re-acetylated product is deacetylated by contact with a deacetylating agent to give free 6,6'-dichloro-6,6'-dideoxysucrose and 1',6,6'-trichloro-1',6,6'-trideoxysucrose.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-09-25 | 1982-03-27 | 1982-09-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-09-25 | 1986-03-27 | 1986-09-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-09-25 | 1990-03-27 | 1990-09-26 | $7700.00 | Window Closed / Lapsed |