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Preparation method of iduronic acid and its derivative

A technology of iduronic acid and its derivatives, which is applied in the field of preparation of iduronic acid and its derivatives, can solve problems such as complicated process, hazards of the surrounding environment, impact on recovery rate, etc., and achieve simple process and reduced harm Effect

Active Publication Date: 2012-07-11
SUZHOU WISMED PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the strong oxidation performance of heavy metal chromium, primary alcohol hydroxyl groups cannot be selectively oxidized, so other hydroxyl groups need to be protected before oxidation, and after oxidation and esterification, deprotection is required, the process is complicated and the recovery rate of the entire reaction is also affected; at the same time Strong acidity and a large amount of heavy metal chromium are used, which are harmful to the human body and the surrounding environment

Method used

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  • Preparation method of iduronic acid and its derivative

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Embodiment Construction

[0010] A preferred preparation method of iduronic acid and derivatives thereof is as follows:

[0011] (1), take 15.5 grams of 3-oxobenzyl-1,2-oxo-isopropylidene-α-D-glucofuranose (molecular weight is 343), dissolve in 150 milliliters of acetonitrile in water (1:1, volume ratio) , under stirring at room temperature, add 0.16 g of TEMPO (molecular weight: 170), then add 37 g of iodobenzenediacetic acid (molecular weight: 322.10), react for 3 hours, add 20 ml of methanol to terminate the reaction; spin dry under reduced pressure.

[0012] The molar ratio of the above-mentioned TEMPO to 3-oxobenzyl-1,2-oxo-isopropylidene-α-D-glucofuran is 0.05, and iodobenzenediacetic acid to 3-oxobenzyl-1,2-oxo-isopropylidene The molar ratio of fork-α-D-glucofuranose is 2.5;

[0013] (2), the product obtained in the above (1) was dissolved in 100 milliliters of DMF (dimethylformamide), 12 grams of anhydrous potassium carbonate was added, and then 10 milliliters of methyl iodide was added, stirr...

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Abstract

The invention provides a preparation method of iduronic acid and its derivative, which is characterized by comprising the following steps: an oxidation method for oxidizing furans glucoside to acid comprises that under the existence of TEMPO (2,2,6,6-tetramethyl-1-piperidine oxide), iodobenzene diacetate is taken as an oxidizing agent for oxidation. The mol ratio of TEMPO to furans glucoside is 0.01-0.1, the mol ratio of oxidizing agent iodobenzene diacetateto to glucofuranose glycoside is 2.0-3.0. The method of the invention has the advantages that furans glucoside primary hydroxyl group is selectively oxidized through a weak oxidizing agent, protection and deprotection for other groups can be omitted, and the technology is simple; heavy metal chromium is not used as the oxidizing agent, thereby harm iduronic acid and its derivative to human body and circumference environment can be minimized during the preparation process.

Description

technical field [0001] The invention relates to a preparation method of iduronic acid and its derivatives, in particular to a chemical synthesis method of iduronic acid and its derivatives. Background technique [0002] Heparin is a mucopolysaccharide extracted from animals, which has anticoagulant and antithrombotic effects. Heparin and heparin derivatives are widely used in the field of medicine. Currently, there are three methods for artificially synthesizing heparin: chemical synthesis, chemical-enzymatic synthesis, and enzymatic synthesis. More than 30 years ago, some European and American scientists established that the effective fragment of heparin is a structure containing iduronic acid when studying the anticoagulant and antithrombotic effects of heparin. [0003] In nature, iduronic acid exists in the form of polysaccharides combined with other sugars, and there is no free iduronic acid. Therefore, to chemically synthesize heparin analogues, iduronic acid must be...

Claims

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Application Information

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IPC IPC(8): C07H7/033C07H1/00
Inventor 王芃
Owner SUZHOU WISMED PHARMA CO LTD