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Method for preparing z-deoxy-D-glucose

A technology of glucose and dideoxy, applied in the direction of deoxy/unsaturated sugar, etc., can solve the problems of low selectivity and low yield, and achieve the effects of good selectivity, good production safety and few by-products

Inactive Publication Date: 2006-10-25
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, this method also has many shortcomings, such as the use of highly toxic benzene and phenylhydrazine, when reducing the carbon-carbon double bond of conjugated nitroalkenes, the selectivity is not high and the yield is low

Method used

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  • Method for preparing z-deoxy-D-glucose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1), the preparation of D-arabo-tetraacetyl-1-nitrohexene-1:

[0029] In 50 ml of n-hexane, add 3.53 grams of 1-nitro-1-deoxy-D-mannose pentaacetate, 3.8 grams of sodium bicarbonate, and react at 60°C; after the reaction is completed, cool, filter, and spin the filtrate under reduced pressure The solvent was removed by evaporation, and the residue was recrystallized from 20-40 ml of ethyl acetate to obtain 2.69 g of a white flaky solid, namely D-arabo-tetraacetyl-1-nitrohexene-1, with a yield of 89.1%.

[0030] 2), the preparation of 1-nitro-1,2-dideoxy-D-arabo-hexose tetraacetate:

[0031] Add 1.85 g of D-arabo-tetraacetyl-1-nitrohexene-1 to 25 ml of solvent (methanol:ether volume ratio 1:1), add 0.15 g of lithium borohydride and 0.50 g of aluminum oxide as an additive; Stir the reaction at 30°C until the raw material disappears, filter, and neutralize the filtrate to PH6-8 with 5% hydrochloric acid by weight, remove the solvent by rotary evaporation under reduced pres...

Embodiment 2

[0036] 1), the preparation of D-arabo-tetraacetyl-1-nitrohexene-1:

[0037] In 50 ml of cyclohexane, add 3.53 grams of 1-nitro-1-deoxy-D-mannose pentaacetate, 4.0 grams of sodium carbonate, and react at 50 ° C; after the reaction is completed, cool, filter, and spin the filtrate under reduced pressure The solvent was removed by evaporation, and the residue was recrystallized through 20-40 ml of ether to obtain 2.52 g of a white flaky solid, ie, D-arabo-tetraacetyl-1-nitrohexene-1, with a yield of 83.4%.

[0038] 2), the preparation of 1-nitro-1,2-dideoxy-D-arabo-hexose tetraacetate:

[0039] Add 1.85 g of D-arabo-tetraacetyl-1-nitrohexene-1 to 30 ml of solvent (methanol:chloroform volume ratio 1:1), add 0.20 g of potassium borohydride, and stir the reaction at 50°C until the raw material disappears , with a weight concentration of 5% hydrochloric acid to neutralize to PH6-8, remove the solvent by rotary evaporation under reduced pressure, add 30 ml of water, extract with chlo...

Embodiment 3

[0044] 1), the preparation of D-arabo-tetraacetyl-1-nitrohexene-1:

[0045] In 50 ml of toluene, add 3.53 grams of 1-nitro-1-deoxy-D-mannose pentaacetate, 4.8 grams of potassium carbonate, and react at 80°C; after the reaction is completed, cool, filter, and remove the filtrate by rotary evaporation under reduced pressure solvent, the residue was recrystallized from 20-40 ml of ethyl acetate-petroleum ether (10 ml of ethyl acetate), and 2.67 g of white flaky solids were obtained, that is, D-arabo-tetraacetyl-1-nitrohexene- 1. The yield is 88.4%.

[0046] 2), the preparation of 1-nitro-1,2-dideoxy-D-arabo-hexose tetraacetate:

[0047] Add 1.85 g of D-arabo-tetraacetyl-1-nitrohexene-1 to 30 ml of solvent (methanol: tetrahydrofuran volume ratio 1:5), add 0.12 g of sodium borohydride, and stir the reaction under reflux until the raw materials disappear. Neutralize to PH6-8 with 5% hydrochloric acid by weight, remove the solvent by rotary evaporation under reduced pressure, add 3...

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Abstract

This invention relates to 2-deoxygenation-D-glucose preparation method. The method is that D-arabinose is reacted with nitromethane, and the reaction prodect is material, 2 bit acetoxy is selective stripped to get nitryl sugar ene. Borohydride isused to selectively reduce conjugated carbon carbon double bond of the sugar ene to get saturated nitryl sugar. Then the goal compound 2-deoxygenation-D-glucose I sogt after Nef reaction. In this invention, the selectivity is good, yield is improved, the material source is wide, cost is low, and its technique design is reasonable.

Description

technical field [0001] The invention belongs to the technical field of resources and medicine and chemical industry, and particularly relates to a chemical preparation method of an anticancer and antibacterial drug 2-deoxy-D-glucose raw material. Background technique [0002] 2-Deoxy-D-glucose is an anti-metabolite of D-glucose, and it is also an important component of the envelope of orthomyxoviruses, paramyxoviruses and herpes viruses. It has the functions of interfering with the synthesis of virus-specific glycoproteins, inhibiting the proliferation of herpes monoviruses, RNA and DNA enveloped viruses, and breast cancer cells. basic structural unit. At present, antiviral and anticancer drugs made of 2-deoxy-D-glucose have been clinically used in the treatment of herpes monovirus and cancer; anti-aging cosmetics and medical and health products made of 2-deoxy-D-glucose have also been used listed. Therefore, as a drug for treating cancer, viral diseases and anti-aging of...

Claims

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Application Information

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IPC IPC(8): C07H3/08
Inventor 郑化岳智洲赵静
Owner WUHAN UNIV OF TECH
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