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Preparation method of beta-glucose-based-Yariv reagent

A technology of glucosyl and glucoside, applied in the fields of chemical industry and medicine, can solve the problems of restricting the application and development of β-D-glucosyl-Yariv reagent, complicated operation, complicated process, etc., and achieves low production cost, low dosage, simple craftsmanship

Inactive Publication Date: 2013-01-23
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above synthetic methods have complicated process, cumbersome operation, and low yield, which is generally about 20% to 40%, which seriously restricts the wide application and development of β-D-glucosyl-Yariv reagent.

Method used

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  • Preparation method of beta-glucose-based-Yariv reagent
  • Preparation method of beta-glucose-based-Yariv reagent
  • Preparation method of beta-glucose-based-Yariv reagent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] a, the preparation of p-aminophenylglucoside

[0025] Get the p-nitrophenyl glucoside 0.10g of 0.33mmol and add 10ml absolute methanol, mix and stir about 5 minutes, then add nickel content and be 0.30g of Raine nickel as metal catalyst of 10% (weight ratio), above-mentioned mixture and Put the Raney nickel catalyst together into the reactor, feed hydrogen with a pressure of 0.3MPa while continuously stirring, and perform a reduction reaction at 80°C for 3 hours. After the conversion is complete, cool to room temperature, filter through diatomaceous earth, and combine the filtrates Concentrate under reduced pressure to obtain p-aminophenyl glucoside, the pressure of the reduced-pressure concentration is 3.5KPa, the temperature is 30°C,

[0026] b, the preparation of diazonium salt

[0027] Dissolve the p-aminophenyl glucoside obtained by concentrating under reduced pressure in 2ml of pure water, then add 1ml of 0.5M hydrochloric acid and sodium nitrite solution dropwis...

Embodiment 2

[0031] a, the preparation of p-aminophenylglucoside

[0032] Get 3.3mmol of p-nitrophenyl glucoside 1.0g and add 90ml of absolute methanol, mix and stir for about 5 minutes, then add 0.20g of palladium catalyst with a palladium content of 10% (weight ratio), put the above mixture and palladium catalyst together into the reactor, feed hydrogen with a pressure of 0.5 MPa while continuously stirring, and perform a reduction reaction at 70°C for 4 hours. After the conversion is complete, cool to room temperature, filter through diatomaceous earth, combine the filtrates and concentrate under reduced pressure to obtain the right For aminophenyl glucoside, the pressure of vacuum concentration is 3.8KPa, and the temperature is 35°C.

[0033] b, the preparation of diazonium salt

[0034] Dissolve the p-aminophenyl glucoside obtained by the above-mentioned concentration under reduced pressure in 2ml of pure water, then add 10ml of 0.5M hydrochloric acid and sodium nitrite solution drop...

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Abstract

The invention discloses a preparation method of a beta-glucose-based-Yariv reagent. The method is characterized in that p-nitrobenzophenone glucoside is taken as a raw material to be synthesized into p-amino-phenyl glucoside, and then reduction, diazotization and coupling reaction are carried out to obtain the beta-glucose-based-Yariv reagent. Compared with the prior art, the method of invention has the advantages of simple process, convenient operation, high yield and low-cost, wherein the raw material used for synthesization is cheap and can be obtained easily and little organic solvent or catalyzer is used. The method is a new glucoside synthesization method with wide application prospects.

Description

technical field [0001] The invention relates to the technical fields of medicine and chemical industry, in particular to a preparation method of β-glucosyl-Yariv reagent. Background technique [0002] β-glucosyl-Yariv reagent (β-D-glucosyl-Yariv reagent, βGlcY), namely: 1,3,5-tris(4-β-D-glucopyranosyl-oxy-phenylazo) -2,4,6-trihydroxybenzene is a synthetic phenyl azo dye, which is of great significance for us to explore the distribution and physiological effects of AGPs in plants. This reagent can be used with arabinogalactose Glycosyls of proteins (AGPs) react to form a red precipitate. [0003] At present, there is no domestic research report on the synthesis technology of 4-β-D-glucopyranosyloxy-oxyphenylazo group. Abroad, the earliest article published by J. Yariv et al. in 1962 (Yariv, J.; Rapport, M.M.; Graf, L. The interaction of glycosides and saccharides with antibody to the corresponding phenyl azo glycoside. Biochem. J.1962, 85 , 383-388.) The synthetic method o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H1/00
Inventor 张剑波李萌陈琛许意达田祥光
Owner EAST CHINA NORMAL UNIV