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Preparation method of 2-deoxy-D-glucose

A technology of glucose and glucosinolate, which is applied in the chemical field, can solve the problems of non-environmental protection and economy, troublesome operation, high cost, etc., and achieve the effect of simple and clear method, low cost and less raw materials

Inactive Publication Date: 2014-07-09
路梦洋
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to solve the problems of low yield, cumbersome operation, non-environmental protection and economical and high cost in the synthesis of 2-deoxy-D-glucose, and provide an environmentally friendly and economical, high yield, simple operation and low-cost preparation method

Method used

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  • Preparation method of 2-deoxy-D-glucose
  • Preparation method of 2-deoxy-D-glucose
  • Preparation method of 2-deoxy-D-glucose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 150 ml of purified water, 10 g of cationic resin, 25.8 g of 3,4,5-tri-O-acetyl D-glucal (0.10 mol) into a 250 ml reaction bottle, react at 25°C-30°C for 24 hours, filter , wash the resin with water, combine the filtered solution and the washing solution, add 1.0 g of medicinal activated carbon to decolorize at room temperature, filter, and concentrate the filtered solution under reduced pressure below 50 ° C, then add 250-350 ml of acetone for recrystallization, filter, and wash with a small amount of acetone , the solid was dried under reduced pressure and vacuum to obtain 11.28 g of 2-deoxy-D-glucose, with a yield of 75.20%.

Embodiment 2

[0033] Add 150 milliliters of purified water, 10 grams of cationic resin, 13.2 grams of 3,4,5-tri-hydroxy-D-glucal (0.10mol) into a 250 milliliter reaction bottle, react at 25°C-30°C for 15 hours, filter, Wash the resin with water, combine the filtered solution and the washing solution, concentrate the filtered solution under reduced pressure below 50°C, then add 250-350 ml of acetone to recrystallize, filter, wash with a small amount of acetone, and dry the solid under vacuum to obtain 2-deoxy-D - Glucose 12.32 grams, yield 82.13%.

[0034] The melting point is 144-147°C.

[0035] H NMR (D 2 O, 400MHz): 4.93(d, 1H), 3.91(d, 1H), 3.g8(d, 1H), 3.81(d, 1H), 3.69-3.74(m, 4H), 3.37-3.41(m, 1H), 3.28(t, 6H), 1.46-1.55(m, 2H).

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Abstract

The invention relates to a preparation method of 2-deoxy-D-glucose, which belongs to the chemical technical field. The preparation method comprises the following steps: taking 3,4,5-tri-O-acetyl D-glucal or 3,4,5-tri-hydroxy-glucal as a raw material, and is placed in a solvent under existence of solid acid, stirring and reacting for certain time under certain temperature, filtering to remove solid acid, washing the solid acid by using the solvent (the recovered solid acid enables repetitive usage), merging and filtering the solvent and then washing the solvent, adding active carbon for decolouring if necessary, filtering and removing the solvent under the pressure reduction condition after filtering the solvent, then adding a recrystallization solvent for recrystallization, cooling and filtering, washing by the recrystallization solvent, and drying under reduced pressure to obtain the white solid product 2-deoxy-D-glucose. The preparation method has the advantages of high yield, simple operation, mild condition, environmental protection, economic, and no pollution, and can be used for industrial production.

Description

technical field [0001] The invention provides a method for preparing 2-deoxyglucose, belonging to the technical field of chemistry. Background technique [0002] 2-Deoxy-D-glucose is an anti-metabolite of D-glucose, which has the effects of interfering with the synthesis of virus-specific glycoproteins, inhibiting herpes monoviruses, RAN and DNA enveloped viruses, and cancer cell proliferation. At present, antiviral and anticancer drugs prepared from 2-deoxy-D-glucose have been clinically used in the treatment of herpes monovirus and cancer, and medical and health products and anti-aging cosmetics prepared from 2-deoxy-D-glucose have also been listed. 2-Deoxy D-glucose has no toxic and side effects, and is widely used in medicine and health care products, anti-aging cosmetics and life science research fields, with huge market potential and good development prospects. [0003] There are many ways to prepare 2-deoxy-D-glucose, and the methods and principles are also different...

Claims

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Application Information

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IPC IPC(8): C07H3/08C07H1/00
Inventor 路梦洋
Owner 路梦洋
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