Method of preparing trichloro sucrose-6-organic acid ester

A technology of organic acid esters and sucrose, applied in organic chemistry, preparation of sugar derivatives, chemical instruments and methods, etc., can solve the problems of large investment and complicated process

Inactive Publication Date: 2007-04-18
HEBEI SUKERUI SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The object of the present invention is to provide a new series of sucrose derivatives with a structure such as formula I that overcomes the defects of large investment and comple

Method used

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  • Method of preparing trichloro sucrose-6-organic acid ester
  • Method of preparing trichloro sucrose-6-organic acid ester
  • Method of preparing trichloro sucrose-6-organic acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1, the synthesis of sucrose-6-ethyl ester

[0023] Take 34.2 grams of sucrose, add it to a four-neck flask equipped with stirring, add 140ml of DMF, raise the temperature to 90°C, stir for 30 minutes, after the sucrose is completely dissolved, cool down to 40°C, add 14 grams of N,N-dimethyl Acetamide dimethyl acetal, after the addition, keep warm at 40-50°C for 2.5 hours, remove part of the solvent under reduced pressure, cool down to below 20°C, add 14ml of water, and adjust the pH of the system to about 6.5 with acetic acid , continue stirring for 30 minutes. Stop responding. Liquid chromatography detection showed that the content of sucrose-6-ethyl ester was 28.3%, and the yield was 85%.

Embodiment 2

[0024] Embodiment 2, the synthesis of sucrose-6-ethyl ester

[0025] Take 20 grams of pulverized sucrose, add it to a four-neck flask equipped with stirring, add 50ml DMF and 40ml pyridine, heat up to 50°C, add dropwise 9.2 grams of N,N-dimethylacetamide dimethyl acetamide under rapid stirring After the addition of aldehyde, keep warm at 40-50°C for 4 hours, remove part of the solvent under reduced pressure, cool down to below 20°C, add 9ml of water, adjust the pH of the reaction mixture to about 6.5 with acetic acid, and continue stirring for 30 minutes. Stop responding. Liquid chromatography detection showed that the content of sucrose-6-ethyl ester was 25.6%, and the yield was 77%.

Embodiment 3

[0026] Embodiment 3, the synthesis of sucrose-6-benzoate

[0027] Take 20 grams of sucrose, add it to a four-necked flask equipped with stirring, add 90ml of DMF, raise the temperature to 90°C, stir for 30 minutes, after the sucrose is completely dissolved, cool down to 40°C, and dropwise add 13 grams of N,N-dimethyl Benzyl benzamide dimethyl acetal, after the addition, keep warm at 40-50°C for 4.5 hours, remove part of the solvent under reduced pressure, cool down to below 20°C, add 9ml of water, adjust the pH value to about 6.5 with acetic acid, Stirring was continued for 30 minutes. Stop responding. As detected by liquid chromatography, the content of sucrose-6-benzoate was 30.5%, and the yield was 82%.

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Abstract

The present invention provides a method for preparing key intermediate-sucrose-6-organic acid ester for preparing trichlorosucrose. Said method includes the following steps: using N,N-dimethylamidodimethylacetal compound and sucrose as raw material, making them produce reaction to form ring, then making hydrolysis so as to obtain the invented sucrose-6-organic acid ester.

Description

technical field [0001] The invention relates to a method for preparing sucrose-6-organic acid ester, a key intermediate in sucralose. Background technique [0002] Sucralose is a new type of sweetener with high sweetness, no calorific value, stable properties, safe use, and excellent comprehensive performance. There are currently three main methods for its synthesis: [0003] 1. Raffinose method, that is, raffinose is used as raw material, chlorinated with thionyl chloride in the presence of triphenylphosphine oxide, then deacetylated, and finally hydrolyzed to sucralose under the action of enzymes. [0004] 2. The whole group protection method, using sucrose as a raw material, reacts with trityl chloride to protect three primary hydroxyl groups, and acetylates with acetic anhydride to obtain 6,1',6'-tri-O-benzyl Base-sucrose penta-acetate, detritylation, transposition of acetyl group, chlorination, deacetylation to obtain sucralose; [0005] 3. The monoester method, that ...

Claims

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Application Information

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IPC IPC(8): C07H15/04C07H15/203
CPCC07H5/04C07H1/00C07H3/04
Inventor 吴俊静吴广利蔡庆海于守信李自文刘晌王满堂
Owner HEBEI SUKERUI SCI & TECH
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