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Preparation method of o-nitrobenzene galactoside

A technology of o-nitrophenyl galactoside and nitrobenzene half, which is applied in the field of sugar engineering, can solve the problems of low yield and incomplete reaction of glycoside products, and achieve the effect of increasing reaction yield and shortening reaction time

Active Publication Date: 2013-02-27
SHENGQUAN HEALTANG
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The prior art discloses a variety of preparation methods of o-nitrophenylgalactosides, such as the document Aryl O-and S-galactosides and lactosides as specific inhibitors of hum an galectins-1 and-3:Role of electrostatic potential at O-3By Giguere, Denis et al From Bioorganic & Medicinal Chemistry Letters, 16 (6), 1668-1672; 2006 discloses by tetraacetylbromogalactose and o-nitrophenol in tetrabutyl ammonium bisulfate and sodium carbonate in water and di Heat reflux in the system of methyl chloride to obtain the glycosylated product, and the glycosylated product is deacetylated by sodium methoxide to obtain the final product, but the reaction for preparing the glycosylated product is not complete, and the yield is low

Method used

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  • Preparation method of o-nitrobenzene galactoside
  • Preparation method of o-nitrobenzene galactoside
  • Preparation method of o-nitrobenzene galactoside

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[0021] The invention provides a preparation method of o-nitrophenylgalactoside, comprising:

[0022] A) Tetraacetylbromogalactose, o-nitrophenol, sodium hydroxide and tetrabutylammonium bromide are heated and reacted in water and dichloromethane to obtain tetraacetyl o-nitrophenylgalactoside;

[0023] B) Deacetylation of tetraacetyl-o-nitrophenylgalactoside to obtain o-nitrophenylgalactoside.

[0024] The present invention uses tetraacetylbromogalactose as the raw material, which has the structure of formula (II), and the present invention has no special limitation on its source, preferably commercially available;

[0025]

[0026] Formula (II).

[0027] The present invention uses o-nitrophenol as a raw material, which has a structure of formula (III), and the present invention has no special limitation on its source, preferably commercially available;

[0028]

[0029] Formula (III).

[0030] The present invention has no special limitation on the source of sodium hyd...

Embodiment 1

[0042] Stir and dissolve 1 mol of tetraacetylbromogalactose and 20 mol of dichloromethane, add 1 mol of tetrabutylammonium bromide, 1 mol of sodium hydroxide, 20 mol of water, and 1 mol of o-nitrophenol into the reaction kettle, reflux at 40.2°C After reacting for 2 hours, a reaction solution was obtained, and thin layer chromatography (TLC) showed that the reaction was complete. The organic phase was separated from the reaction solution, evaporated to dryness, recrystallized by adding 1.5 mol of ethanol, and dried to obtain 0.876 mol of tetraacetyl-o-nitrophenylgalactoside.

[0043] Add 0.876 mol of tetraacetyl-o-nitrophenylgalactoside prepared above, 1.5 mol of methanol, and 0.01 mol of sodium methoxide into the reaction kettle, stir and react at room temperature for 2 hours to obtain a reaction liquid, which is detected by TLC and the reaction is complete. Add 0.01 mol of acetic acid to neutralize the reaction solution, evaporate to dryness, filter and dry to obtain 0.781 m...

Embodiment 2

[0046] Stir and dissolve 1 mol of tetraacetylbromogalactose and 20 mol of dichloromethane, add 1 mol of tetrabutylammonium bromide, 1.1 mol of sodium hydroxide, 20 mol of water, and 1 mol of o-nitrophenol into the reaction kettle, and condense at 40.2°C Reflux reaction for 2 hours to obtain a reaction solution, TLC showed that the reaction was complete. Separate the organic phase from the reaction solution, evaporate the organic phase to dryness, add 1.5 mol of ethanol, recrystallize and dry to obtain 0.882 mol of tetraacetyl-o-nitrophenylgalactoside.

[0047] Add 0.882 mol of tetraacetyl-o-nitrophenylgalactoside prepared above, 1.5 mol of methanol, and 0.01 mol of sodium methoxide into the reaction kettle, stir and react at room temperature for 2 hours, and obtain the reaction solution. After TLC detection, the reaction is complete. Add 0.01 mol of acetic acid neutralized the reaction liquid, evaporated to dryness, filtered, and dried to obtain 0.783 mol of the reaction produ...

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Abstract

The invention provides a preparation method of o-nitrobenzene galactoside, which comprises the following steps: performing heating reaction on tetra-acetylated bromogalactose, o-nitrophenol, sodium hydroxide and tetrabutyl ammonium bromide in water and dichloromethane to obtain tetra-acetylated o-nitrobenzene galactoside; and performing deacetylation on the tetra-acetylated o-nitrobenzene galactoside to obtain the o-nitrobenzene galactoside. According to the invention, the tetra-acetylated bromogalactose and the o-nitrophenol react in a system of the tetrabutyl ammonium bromide and the sodium hydroxide, and the presence of the tetrabutyl ammonium bromide and the sodium hydroxide ensures that the o-nitrophenol and the tetra-acetylated bromogalactose react more thoroughly, thereby shortening the reaction time and improving the reaction yield.

Description

technical field [0001] The invention relates to the technical field of sugar engineering, in particular to a preparation method of o-nitrophenylgalactoside. Background technique [0002] O-nitrophenylgalactoside has a structure of formula (I), can be used as a chromogenic substrate for β-galactosidase, and has wide application value in the field of biological detection. [0003] [0004] Formula (I) [0005] The prior art discloses a variety of preparation methods of o-nitrophenylgalactosides, such as the document Aryl O-and S-galactosides and lactosides as specific inhibitors of hum an galectins-1 and-3:Role of electrostatic potential at O-3By Giguere, Denis et al From Bioorganic & Medicinal Chemistry Letters, 16 (6), 1668-1672; 2006 discloses by tetraacetylbromogalactose and o-nitrophenol in tetrabutyl ammonium bisulfate and sodium carbonate in water and di Heat reflux in the system of methyl chloride to obtain the glycosylated product, and the glycosylated product is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H1/00
Inventor 江成真孔令华
Owner SHENGQUAN HEALTANG
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