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Process for selectively synthesizing sucrose-6-ester

A selective, sucrose-based technology, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of difficult organotin recovery, cumbersome operation, complicated process, etc., and achieves convenient and easy synthesis method and excellent preparation process. Simplicity and the effect of reducing production costs

Inactive Publication Date: 2008-10-22
CHANGZHOU NIUTANG CHEM PLANT CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the process is complicated, the operation is cumbersome, and the recovery of highly toxic organotin is difficult.

Method used

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  • Process for selectively synthesizing sucrose-6-ester
  • Process for selectively synthesizing sucrose-6-ester
  • Process for selectively synthesizing sucrose-6-ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Synthesis of sucrose-6-acetate with N-acetyl-2-thiazolethione

[0025] 1.1 Synthesis of N-acetyl-2-thiazolethione

[0026] Add 10mmol 2-thiazolethione and 25mL dichloromethane into a 150mL three-neck flask, stir to dissolve, add 2.4mL triethylamine, stir and cool to 0°C under an ice-water bath. Then, a mixture of 15 mmol acetyl chloride and 5 mL of anhydrous dichloromethane was added dropwise to the reaction solution, and the reaction temperature was kept below 5° C. during the dropwise addition. After the dropwise addition, it was raised to room temperature and reacted for 2 hours. TLC monitoring showed that the reaction was completed. Add 0.5N hydrochloric acid solution to neutralize, then add 5% sodium bicarbonate solution to wash until neutral, separate the liquids to obtain an organic phase, and dry with anhydrous magnesium sulfate. , filtered, and the solvent was distilled off to obtain N-acetyl-2-thiazolethione as a light yellow liquid with a crude yi...

Embodiment 2

[0029] Example 2: Synthesis of sucrose-6-propionate with N-propionyl-2-thiazolethione

[0030] 2.1 Synthesis of N-propionyl-2-thiazolethione

[0031] Add 10mmol 2-thiazolethione and 25mL dichloromethane into a 150mL three-neck flask, stir to dissolve, add 2.4mL triethylamine, stir and cool to 0°C under an ice-water bath. Then, a mixture of 15 mmol propionyl chloride and 5 mL of anhydrous dichloromethane was added dropwise to the reaction solution, and the reaction temperature was kept below 5° C. during the dropwise addition. After the dropwise addition, the mixture was raised to room temperature and reacted for 2 hours. TLC monitoring showed that the reaction was complete. Add 0.5N hydrochloric acid solution to neutralize, then add 5% sodium bicarbonate solution to wash until neutral, separate the liquids to obtain an organic phase, and dry it with anhydrous magnesium sulfate. After filtration, the solvent was distilled off to obtain N-propionyl-2-thiazolethione as light yel...

Embodiment 3

[0034] Example 3: Synthesis of sucrose-6-acetate with N-acetylbenzotriazole

[0035] 3.1 Synthesis of N-acetylbenzotriazole

[0036] Add 10mmol benzotriazole and 25mL dichloromethane into a 150mL three-neck flask, stir to dissolve, add 2.4mL triethylamine, stir and cool to 0°C under an ice-water bath. Then, a mixture of 15 mmol acetyl chloride and 5 mL of anhydrous dichloromethane was added dropwise to the reaction solution, and the reaction temperature was kept below 5° C. during the dropwise addition. After the dropwise addition, the mixture was raised to room temperature and reacted for 2 hours. TLC monitoring showed that the reaction was complete. Add 0.5N hydrochloric acid solution to neutralize, then add 5% sodium bicarbonate solution to wash until neutral, separate the liquids to obtain an organic phase, and dry it with anhydrous magnesium sulfate. After filtration, the solvent was distilled off to obtain N-acetylbenzotriazole in the form of light yellow liquid, with a...

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Abstract

The invention provides a method for selectively synthesizing sugar-6-ester; wherein, firstly, the secondary amine or oxime (R'H) of five-member ring reacts with acyl chloride (RCOCl) and triethylamine in the environment of aprotic solvent and active amide or active ester is obtained; then the raw material of sugar, the acylating reagent of the prepared active amide or active ester and the catalyst of the triethylamine are stirred and react at indoor temperature, and after the reaction is finished, a base catalyst of intra-molecular shift is added to make the shift of intra-molecular acyl; finally, adhesive column chromatography is adopted for separation to obtain the sugar-6-ester of 6-bit mono-protection. The synthetic method is convenient and simple in operation and the product is high in purity; the heterocyclic parts of 2-thiazole thione, benzotriazole, etc., of the acylating reagent can be recycled, which reduces the production cost of the sugar-6-ester and has a very good practical application meaning for the fields of surfactants, food additives, insecticides, etc.

Description

technical field [0001] The invention relates to a method for selectively synthesizing sucrose-6-ester. The prepared monoester has high purity and can be used to prepare high-grade sweetener sucralose, belonging to the technical field of fine chemicals. Background technique [0002] Sucrose esters are widely used in surfactants, food additives, pesticides and other products. Among them, the sucrose with the 6-hydroxyl group protected alone is the focus of current research. It is not only a key intermediate in the synthesis of the high-efficiency sweetener sucralose, but also has good surface activity and biological activity. Because the activities of the eight hydroxyl groups on the sucrose molecule are similar, and the acyl groups on the sucrose are prone to intramolecular migration, the sucrose esters usually synthesized are mixtures of monoesters, diesters and polyesters, and also contain a large amount of isocomponents. isomer. It is very difficult to obtain selective m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/04C07H13/08
Inventor 方志杰郑保障王方大叶磊蔡亚陈凯
Owner CHANGZHOU NIUTANG CHEM PLANT CO LTD
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