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Method for synthesizing uronic acid through catalytic oxidation of pyranoside

A pyranoside, catalytic oxidation technology, applied in chemical instruments and methods, sugar compounds with non-glycosyl groups, organic chemistry, etc., can solve the problems of high processing difficulty, complicated operation, human interference, etc., to improve reaction efficiency, The effect of simplifying the reaction process

Active Publication Date: 2021-07-16
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Aiming at the problems that the pH of the reaction system must be controlled to be 10 in the existing uronic acid synthesis process, which makes the operation complicated, the human interference is serious, and the product post-treatment is difficult, the present invention provides a method for catalyzing the oxidation of pyranoside to synthesize uronic acid

Method used

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  • Method for synthesizing uronic acid through catalytic oxidation of pyranoside
  • Method for synthesizing uronic acid through catalytic oxidation of pyranoside
  • Method for synthesizing uronic acid through catalytic oxidation of pyranoside

Examples

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Embodiment 1

[0031] The embodiment of the present invention provides a method for catalytic oxidation of methyl-α-D-glucopyranoside to obtain methyl-α-D-glucopyranose acid. The specific reaction process is as follows:

[0032]

[0033] In a 50mL three-neck round bottom flask, add methyl-α-D-glucopyranoside 0.39g (2mmol), TEMPO 0.016g (0.1mmol) and water 10mL in sequence;

[0034] Add 0.31 g (2.2 mmol) of calcium hypochlorite solids in batches at a temperature of 0° C., and the addition time is 10 minutes. After the addition is completed, the catalytic oxidation reaction is carried out, and the reaction time is 4 hours;

[0035] After the reaction is complete, let stand to separate layers, filter under reduced pressure, adjust the pH of the obtained filtrate to 2 with 4mol / L HCl, concentrate under reduced pressure to remove solvent water, add 8 mL of methanol to the obtained concentrate, shake and filter to remove inorganic salts , the obtained filtrate was rotary evaporated to remove th...

Embodiment 2

[0038] The embodiment of the present invention provides a method for catalytic oxidation of methyl-α-D-galactopyranoside to obtain methyl-α-D-galactopyranuronic acid. The specific reaction process is as follows:

[0039]

[0040]In a 50mL three-neck round bottom flask, add methyl-α-D-galactopyranoside 0.39g (2mmol), TEMPO 0.016g (0.1mmol) and water 40mL in sequence;

[0041] Add calcium hypochlorite solid 0.43g (3mmol) in batches under the condition of 10°C, and the addition time is 10min. After the addition is completed, carry out the catalytic oxidation reaction, and the reaction time is 3h;

[0042] After the reaction is complete, let stand to separate layers, filter under reduced pressure, adjust the pH of the obtained filtrate to 3 with 3mol / L HCl, concentrate under reduced pressure to remove solvent water, add 8 mL of ethanol to the obtained concentrate, shake and filter to remove inorganic salts , the obtained filtrate was rotary evaporated to remove the solvent, and...

Embodiment 3

[0045] The embodiment of the present invention provides a method for catalytic oxidation of methyl-α-D-mannopyranoside to obtain methyl-α-D-mannopyranuronic acid, the specific reaction process is as follows:

[0046]

[0047] In a 50mL three-neck round bottom flask, add methyl-α-D-mannopyranoside 0.39g (2mmol), TEMPO 0.032g (0.02mmol) and water 30mL in sequence;

[0048] Add calcium hypochlorite solid 0.57g (4mmol) in batches under the condition of 20 DEG C, the feeding time is 10min, and the catalytic oxidation reaction is carried out after the feeding is completed, and the reaction time is 1h;

[0049] After the reaction is complete, let stand to separate layers, filter under reduced pressure, adjust the pH of the obtained filtrate to 2 with 5mol / L HCl, concentrate under reduced pressure to remove solvent water, add 8 mL of methanol to the obtained concentrate, shake and filter to remove inorganic salts , the obtained filtrate was rotary evaporated to remove the solvent, ...

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Abstract

The invention relates to the technical field of chemical synthesis, and particularly discloses a method for synthesizing uronic acid through catalytic oxidation of pyranoside. According to the method, pyranoside serves as a raw material, TEMPO serves as a catalyst, Ca(OCl)2 serves as an oxidizing agent, catalytic oxidation reaction is carried out in water to obtain uronic acid, the ratio of the amount of pyranoside to the amount of TEMPO is 1: (0.01-0.1), and the ratio of the amount of pyranoside to the amount of Ca(OCl)2 is 1: (1.1-2). In the reaction process, an acid-base regulator does not need to be additionally added, reagent types and dosage required by a reaction system are reduced, the reaction process is simplified, errors and interference caused by human factors are avoided, inorganic salt generated by the reaction system can be greatly reduced, purification and separation of uronic acid are facilitated, the method better conforms to the concept of atom economic chemistry, and the method is more suitable for industrial popularization.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for catalytically oxidizing pyranosides to synthesize uronic acid. Background technique [0002] The key to the synthesis of uronic acid structure is to selectively oxidize the primary hydroxyl group in the glycoside molecule to carboxylic acid. At present, the environment-friendly 2,2,6,6-tetramethylpiperidine oxide (TEMPO) and hypochlorous acid are mainly used. Salt forms a cyclic oxidation system to oxidize glycoside molecules. Compared to NaClO in solution, solid Ca(OCl) 2 It also has the advantages of stable properties, easy operation, good controllability, etc., which are suitable for industrial scale production, so TEMPO and Ca(OCl) are mainly used 2 Form a cyclic oxidation system. But TEMPO-Ca(OCl) 2 The catalytic oxidation combination must not only be carried out in an alkaline environment, but also need to control the pH of the reaction system to...

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H1/06C07H7/033
CPCC07H1/00C07H1/06C07H7/033
Inventor 刘文清王亚军
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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