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Preparation method of 2-deoxidizing-D-glucose

A technology of glucose and glucone, applied in the field of preparation of 2-deoxy-D-glucose, can solve the problems of high cost, unsuitable for large-scale production and promotion, complicated steps and the like, and achieves low production cost, high yield, and high technology simple effect

Inactive Publication Date: 2011-09-14
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The steps of the above synthetic method are cumbersome and costly, and are not suitable for large-scale production and promotion.

Method used

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

Examples

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Embodiment 1

[0027] a, the preparation of intermediates

[0028] Dissolve 1.08g of acetylglucosene in 5mL of dichloromethane, cool in an ice bath to 0°C, keep for 15 minutes, then remove the ice bath, and add hydrogen bromide / acetic acid (HBr / HOAc) with a concentration of 30% by mass in sequence Solution 0.2mL and acetic anhydride 10mL, stirred at 22°C for 24 hours for selective addition reaction, after the reaction was completed, add anhydrous sodium acetate to neutralize to pH = 7, stirred for 20 minutes, filtered and then evaporated under reduced pressure. The steaming temperature is 25°C and the pressure is 0.1MPa. The obtained solid is recrystallized with a solvent mixed with 10mL of petroleum ether and ethyl acetate at a volume ratio of 1:4, and then filtered and vacuum-dried under reduced pressure to obtain a white solid 2- Deoxy-1,3,4,6-tetra- O -Acetyl-D-glucose 1.30g, yield 99%.

[0029] b. Synthesis of 2-deoxy-D-glucose

[0030] Take the intermediate 2-deoxy-1,3,4,6-tetra- O...

Embodiment 2

[0032] a, the preparation of intermediates

[0033] Dissolve 10.0 g of acetylglucosene in 50 mL of tetrahydrofuran, cool in an ice bath to 0°C, and keep for 50 minutes. Acetic anhydride 100mL, stirred at 30°C for 13 hours for selective addition reaction, after the reaction was completed, 50% (weight percent) sodium hydroxide was added to neutralize to pH = 7, stirred for 40 minutes, filtered and then rotary evaporated under reduced pressure, The rotary evaporation temperature is 25°C, the pressure is 0.1MPa, the obtained solid is recrystallized with 100mL of n-hexane and diethyl ether in a volume ratio of 1:4, and then filtered and vacuum-dried under reduced pressure to obtain a white solid 2-deoxy -1,3,4,6-four- O -Acetyl-D-glucose 10.9g, yield 90%.

[0034] b. Synthesis of 2-deoxy-D-glucose

[0035] Take the intermediate 2-deoxy-1,3,4,6-tetra- O Add 5.0 g of -acetyl-D-glucose to 20 mL of sulfuric acid with a concentration of 60% for acid-catalyzed hydrolysis reaction. Th...

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Abstract

The invention discloses a preparation method of 2-deoxidizing-D-glucose, which is characterized in that in the method, an intermediate 2-deoxidizing-1,3,4,6-tetra-O-acetyl group-D-glucose is prepared by the selective addition reaction of acetyl glucose alkene, and acetyl groups are removed by the acid catalytic hydrolysis reaction of an intermediate 2-deoxidizing-acetyl groups-D-glucose, thus obtaining the 2-deoxidizing-D-glucose after purification. Compared with the prior art, the preparation method has the advantages of simple process, good selectivity, high yield and low cost, thus being a relatively green, environment-protective, economical and efficient synthesis method with broad application prospect.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a method for preparing 2-deoxy-D-glucose for producing anticancer and antibacterial active drugs. Background technique [0002] 2-Deoxy-D-glucose is a derivative of D-glucose, which is an antimetabolite (Woodward, 1954, Cancer Res. 14:599-605), is also an important component of orthomyxovirus, paramyxovirus and herpes virus envelope, which can interfere with the synthesis of virus-specific glycoprotein, and can effectively inhibit herpes monovirus, RNA and DNA enveloped virus, mammary gland virus Cancer cell proliferation and other effects (Aft, 2002, Br. J. Cancer. 87:805-812). Antiviral and anticancer drugs made of 2-deoxy-D-glucose have been used in clinical research on herpes monovirus, influenza, AIDS and cancer (Tidmarsh, 3 Nov.2005 PCT US 05 / 0245462); by 2 -Anti-aging cosmetics and medical health products made of deoxy-D-glucose are also on the m...

Claims

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Application Information

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IPC IPC(8): C07H3/08C07H1/00
Inventor 张剑波杨国方魏芳王庆兵
Owner EAST CHINA NORMAL UNIVERSITY
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