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New method for preparing 2-deoxy-D-glucose

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

Inactive Publication Date: 2009-12-23
YUHUAN MARINE BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The present invention also provides a new method for preparing 2-deoxy-D-glucose aiming at 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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Examples

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Embodiment 1

[0049] (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.

[0050] (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

[0056] 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

[0058] 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 provides a new method for preparing 2-deoxy-D-glucose, which belongs to the technical field of resources, medicine and chemical industry. It solves the problems of complex production process and high production cost in the existing 2-deoxy-D-glucose preparation method. The new method for preparing 2-deoxy-D-glucose comprises the following steps: 1, the preparation of 2-deoxy-2-benzylidene amino-D-glucose; 2, 2-deoxy-2-benzylidene amino- Preparation of 3,4,5,6-tetra-O-acetyl-D-glucose; Preparation of 3,2-deoxy-2-amino-3,4,5,6-tetra-O-acetyl-D-glucose Preparation; Preparation of 4, 2-deoxy-2-chloro-3,4,5,6-tetra-O-acetyl-D-glucose; 5, 2-Deoxy-3,4,5,6-tetra-O - Preparation of acetyl-D-glucose; 6. Preparation of 2-deoxy-D-glucose. The preparation method of the invention has wide sources of raw materials, low price, easy operation and great economic, social and environmental benefits.

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 Patents(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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