US4380476A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose (TGS)
Assignee: Tate and Lyle PLC
•
Filing: 1981-06-19
•
Granted: 1983-04-19
•
Expires: 2001-06-19
Abstract
Abstract A process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose (TGS) comprising the steps of: (a) reacting sucrose with an acylating reagent under conditions to provide a mixture of acylated sucrose derivatives containing a major proportion of 6-monoacylated material; (b) optionally separating 6-monoacylated sucrose derivative from other acylated derivatives before step (c); (c) reacting the monoacylated sucrose derivative with a chlorinating reagent capable of chlorinating at positions 1', 4 and 6' of a sucrose 6- acylate; and (d) deacylating and separating (in either order) the 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose material formed.
Inventors
- 👤 Khizar S. Mufti
- 👤 Riaz A. Khan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 10:07
CPC Classifications
C; C07; C07H; C07H5/00; C07H5/02
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
67 words
A process for the preparation of 4,l',6'-trichloro-4,1',6'-trideoxygalactosucrose (TGS) comprising the steps of: (a) reacting sucrose with an acylating reagent under conditions to provide a mixture of acylated sucrose derivatives containing a major proportion of 6-monoacylated material; (b) reacting the monoacylated sucrose derivative with a chlorinating reagent capable of chlorinating at positions 1',4 and 6' of a sucrose 6-acylate; and (c) deacylating and separating the 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose material formed.
Claim 2
Dependent Claim
67 words
A process for the preparation of 4,l',6'-trichloro-4,1',6'-trideoxygalactosucrose (TGS) comprising the steps of: (a) reacting sucrose with an acylating reagent under conditions to provide a mixture of acylated sucrose derivatives containing a major proportion of 6-monoacylated material; (b) reacting the monoacylated sucrose derivative with a chlorinating reagent capable of chlorinating at positions 1',4 and 6' of a sucrose 6-acylate; and (c) deacylating and separating the 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose material formed.
Claim 3
Dependent Claim
41 words
The process of claim 1, wherein the acylating reagent in step (a) is selected from the group consisting of carboxylic acyl anhydrides, carboxylic acyl halides, and enyl acylates and lower alkyl fatty acid esters in the presence of a transesterification catalyst.
Claim 4
Dependent Claim
17 words
The process of claim 1, wherein the acylating reagent is acetic anhydride in a tertiary amine base.
Claim 5
Dependent Claim
24 words
The process of claim 3, wherein the step (a) is effected using acetic anhydride in pyridine at a temperature of -20° to -75° C.
Claim 6
Dependent Claim
25 words
The process of claim 1, wherein the chlorinating reagent in step (b) is selected from the group consisting of a Vilsmeier reagent and sulphuryl chloride.
Claim 7
Dependent Claim
35 words
The process of claim 5, wherein the chlorinating reagent is a Vilsmeier reagent of the formula: [XClC═NR.sub.2 ].sup.+ Cl.sup.- (where R represents an alkyl group, and X represents a hydrogen atom or a methyl group).
Claim 8
Dependent Claim
17 words
The process of claim 6, wherein the chlorinating reagent is prepared by reacting phosphorus pentachloride with N,N-dimethylformamide.
Claim 9
Dependent Claim
20 words
The process of claim 1 in which the 6-monoacylated sucrose derivative is separated from other acylated derivatives before step (b).
Claim 10
Dependent Claim
20 words
The process of claim 8, wherein the separation of acylated material before step (b) is effected using ion-exchange resin chromatography.
Claim 11
Dependent Claim
22 words
The process of claim 9, wherein the resin used is a polystyrene sulphuric acid cation exchanged resin used in the base form.
Claim 12
Dependent Claim
18 words
The process of claim 1, wherein the chlorinated material from step (b) is peracylated before separation and purification.
Claim 13
Dependent Claim
25 words
The process of claim 11, wherein the chlorinated material obtained after hydrolysis of the chlorinating agent is peracetylated in situ using acetic anhydride in pyridine.
Claim 14
Dependent Claim
16 words
The process of claim 1 wherein the separation in step (c) is effected before the deacylation.
Claim 15
Dependent Claim
106 words
A process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose (TGS) comprising the steps of: (a) reacting sucrose with acetic anhydride in pyridine at a temperature below about -20° C. in order to obtain a mixture containing a major proportion of sucrose 6-acetate; (b) separating the sucrose 6-acetate by ion-exchange resin chromatography; (c) chlorinating the sucrose 6-acetate at the 4,1' and 6' positions with a reagent selected from the group consisting of a Vilsmeier reagent and sulphuryl chloride; (c1) peracetylating the chlorinated product with acetic anhydride in pyridine to form TGS penta-acetate; and (d) separating and purifying the TGS penta-acetate and subsequently deacetylating the purified material to obtain TGS.
Claim 16
Dependent Claim
106 words
A process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose (TGS) comprising the steps of: (a) reacting sucrose with acetic anhydride in pyridine at a temperature below about -20° C. in order to obtain a mixture containing a major proportion of sucrose 6-acetate; (b) separating the sucrose 6-acetate by ion-exchange resin chromatography; (c) chlorinating the sucrose 6-acetate at the 4,1' and 6' positions with a reagent selected from the group consisting of a Vilsmeier reagent and sulphuryl chloride; (c1) peracetylating the chlorinated product with acetic anhydride in pyridine to form TGS penta-acetate; and (d) separating and purifying the TGS penta-acetate and subsequently deacetylating the purified material to obtain TGS.
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) | 1986-04-18 | 1986-10-18 | 1987-04-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-04-18 | 1990-10-18 | 1991-04-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-04-18 | 1994-10-18 | 1995-04-19 | $7700.00 | Window Closed / Lapsed |