New method for preparing 2-deoxy-D-glucose

A technique of glucose and a new method, which is applied in the fields of anti-cancer, drug preparation, and chemical preparation of 2-deoxy-D-glucose, an antibacterial drug raw material drug, can solve the problems of 2-deoxy-D-glucose racemization, 2-deoxy - Low yield of D-glucose, complex production process and other problems, to achieve the effect of low price, novel design, reasonable and feasible, and strong antiviral effect

Inactive Publication Date: 2006-05-24
YUHUAN MARINE BIOCHEM
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0007] The present invention also provides a new method for preparing 2-deoxy-D-glucose in view of the problems of many side reactions in the production of 2-deoxy-D-glucose in the prior art, resulting in low yield and low product purity;
[0008] The present invention also solves the problem that the prior art production process is complicated, the production cost is high, and 2-deoxy-D-glucose is easily racemized, and the yield of the prepared 2-deoxy-D-glucose is low, which cannot satisfy the growing market The problem of demand Provide a new method for preparing 2-deoxy-D-glucose that is novel, unique, reasonable and feasible, easy to obtain raw materials, easy to operate, has good production value and wide application prospects

Method used

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  • New method for preparing 2-deoxy-D-glucose
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Examples

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Embodiment 1

[0052] (1) Dissolve 4.0g of sodium hydroxide in 100mL of water, cool in an ice-salt bath to 0°C, add 10.8g of 2-deoxy-2-amino-D-glucose hydrochloride under stirring, the solid is completely dissolved, and a light yellow color is obtained Clear and transparent solution. 5.3 g of benzaldehyde was added at 0°C, and a large amount of white solid 2-deoxy-2-benzylideneamino-D-glucose was formed. After 2 hours of reaction, the white solid 2-deoxy-2-benzylideneamino-D-glucose was washed with water, filtered, and the obtained filter cake was dried under reduced pressure at 50°C to obtain a white powder of 2-deoxy-2- 12.1 g of benzylidene amino-D-glucose was directly used in the acetylation reaction.

[0053] (2) To 100 mL of acetic anhydride, add 10.7 g of 2-deoxy-2-benzylideneamino-D-glucose, the product of step (3), and 10.8 g of sodium acetate, and react at room temperature for 2 hours. The solvent was evaporated under reduced pressure below 30°C, the obtained residue was added to...

Embodiment 2

[0059] Under the condition that the reaction temperature, the concentration of the reactant, and the feeding method are unchanged, the feeding of the reactants in each step in Example 1 is scaled up by 5 times, and the yield and total yield of each step are basically the same as in Example 1.

Embodiment 3

[0061] Adopt the same operating process as Example 1, in step (1) replace sodium hydroxide 4.0g, 100ml ethanol with potassium hydroxide 7.0g to replace 100ml water, p-methyloxybenzaldehyde 6.5g replace benzaldehyde 5.3g, react 1 hour, the reaction temperature is 50 ℃, in step (2) with triethylamine 26.8g instead of sodium acetate 10.8g, acetic acid instead of acetic anhydride as reaction medium, react for 4 hours, reaction temperature 20 ℃, two-step yield 68.2% , in step (3), sulfuric acid-aqueous solution replaces hydrochloric acid-methanol solution, and reaction temperature is 10 ℃; In step (4), KNO 2 instead of NaNO 2 , replace 90ml tetrahydrofuran / ethanol solution with 100ml water / methanol solution in step (5), replace 1.3g sodium borohydride with 1.8g potassium borohydride, react for 2 hours, yield 95.1%; Replace with methanol in step (6) Ethanol was used as the extraction solvent, the reaction temperature was 30°C, and the mass yield was 43.2%.

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Abstract

The invention discloses a method of preparing 2-deoxidation-D-glucose. It solves the problems of the complex manufacturing technique and high cost for existing 2-deoxidation-D-glucose. The method includes the following steps: preparing 1.2-deoxidation-2-phenylenemethylamino-D-glucose; preparing 2.2-deoxidation-2- phenylenemethylamino-3,4,5,6-four-O-acetyl-D-glucose; preparing 4.2-deoxidation -2-chorine-3,4,5,6-four-O-acetyl-D-glucose; preparing 5.2-deoxidation-3,4,5,6- four-O-acetyl-D-glucose; preparing 6.2-deoxidation-D-glucose. The raw material of the method is far ranging, and low cost. It has great economic, social, and environment benefit.

Description

technical field [0001] The invention relates to a preparation method of medicine, in particular to a chemical preparation method of 2-deoxy-D-glucose, an anticancer and antibacterial drug raw material; it belongs to the technical field of resources, medicine and chemical industry. Background technique [0002] 2-Deoxy-D-glucose is a derivative of D-glucose, the English name is 2-Deoxy-D-glucose (abbreviated as 2DG), the chemical structure formula is: [0003] [0004] 2-Deoxy-D-glucose is a lactone antibiotic and anti-metabolite. It is an important component of the envelope of orthomyxoviruses, paramyxoviruses and herpes viruses. It can interfere with the synthesis of virus-specific glycoproteins and effectively inhibit herpes single Viruses, RNA and DNA enveloped viruses, breast cancer cell proliferation, etc. Antiviral and breast cancer drugs made from 2-deoxy-D-glucose have been used in herpes monovirus, influenza, Sars, AIDS and cancer clinical treatment research; an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H3/08
Inventor 郑化岳智洲徐君义林荣业
Owner YUHUAN MARINE BIOCHEM
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