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Double-arm heterogeneous sugar-containing compound and preparation method thereof

A compound and double-arm technology, applied in the field of double-arm sugar-containing compound synthesis, can solve the problems of reducing product yield and increasing reaction steps, and achieve the effect of stable synthesis method

Pending Publication Date: 2022-07-15
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the artificially synthesized sugar-containing compounds are all reacted with the sugar containing the protective group and then removed the protective group. This method not only increases the reaction steps, but also greatly reduces the yield of the obtained product.

Method used

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  • Double-arm heterogeneous sugar-containing compound and preparation method thereof
  • Double-arm heterogeneous sugar-containing compound and preparation method thereof
  • Double-arm heterogeneous sugar-containing compound and preparation method thereof

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preparation example Construction

[0073] The present invention provides a method for preparing a double-armed heterogeneous sugar-containing compound, comprising the following steps:

[0074] (1) aniline substitution reaction occurs with external norbornene dianhydride and p-bromoaniline, and aftertreatment obtains the first compound;

[0075] (2) The first compound obtained in step (1), together with Pd(PPh 3 ) 4 , anhydrous sodium carbonate and 4-hydroxyphenylboronic acid take place Suzuki coupling reaction, and after-treatment obtains the second compound;

[0076] (3) the second compound that step (2) obtains and triethylamine, isopropylidene-2,2-bis (oxymethyl) propionic anhydride and 4-dimethylaminopyridine generate the esterification reaction of hydroxyl and acid anhydride, After treatment, the third compound is obtained;

[0077] (4) The third compound obtained in step (3) and Dowex-H + The hydrolysis reaction of the ketal occurs, and the aftertreatment obtains the fourth compound;

[0078] (5) the...

Embodiment 1

[0114] This embodiment provides a double-armed heterogeneous sugar-containing compound and a preparation method thereof.

[0115] (1) Synthesis of the first compound

[0116] cis-5-norbornene-exo-2,3-dicarboxylic acid anhydride (20 g, 0.122 mol) was placed in a dry round bottom flask, and acetic acid 140 mL was added. The mixture was heated to 120°C until cis-5-norbornene-exo-2,3-dicarboxylic anhydride was dissolved and 4-bromoaniline (25.2 g, 0.146 mol) was added. The reaction was carried out at 120°C for 0.5h. After the reaction was completed, it was poured into ice water to form a white precipitate. The monomer was extracted with dichloromethane, washed with distilled water and dried. 29 g of a white solid (ie, the first compound) was obtained in a yield of 75%.

[0117] The H NMR spectrum of the first compound is as follows figure 1 shown;

[0118] The chemical structural formula of the first compound is shown below:

[0119]

[0120] The NMR data for the first c...

Embodiment 2

[0165] This embodiment provides a double-armed heterogeneous sugar-containing compound and a preparation method thereof.

[0166] (1) Synthesis of the first compound

[0167] cis-5-norbornene-exo-2,3-dicarboxylic acid anhydride (20 g, 0.122 mol) was placed in a dry round bottom flask, and acetic acid 140 mL was added. The mixture was heated to 120°C after cis-5-norbornene-exo-2,3-dicarboxylic anhydride was dissolved and 4-bromoaniline (20.74 g, 0.122 mol) was added. The reaction was carried out at 130 °C for 1 h. After the reaction was completed, it was poured into ice water to form a white precipitate. The monomer was extracted with dichloromethane, washed with distilled water and dried. 30 g of a white solid (ie, the first compound) was obtained in a yield of 79%.

[0168] The chemical structural formula of the first compound is shown below:

[0169]

[0170] (2) Synthesis of the second compound

[0171] A nitrogen purge with the first compound (10 g, 31.4 mmol) and...

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Abstract

The invention relates to the technical field of synthesis of two-armed sugar-containing compounds, in particular to a two-armed heterogeneous sugar-containing compound and a preparation method thereof. The preparation method comprises the following steps: firstly, enabling external norbornene anhydride to react with 4-bromoaniline, replacing oxygen in the external norbornene anhydride with amino, then forming a biphenyl compound by utilizing Suzuki reaction, then reacting with isopropylidene-2, 2-bis (oxymethyl) propionic anhydride by utilizing esterification reaction, and introducing dihydroxyl under an acidic condition through deprotection; then carrying out esterification reaction and pentyne anhydride reaction to obtain a dialkyne compound; and carrying out a CuAAC reaction with nitrine sugar to prepare the double-arm heterogeneous sugar-containing compound. Compared with the prior art, the method has the advantages that the two-arm terminal alkyne-containing compound is synthesized by utilizing the advantages of the Suzuki reaction, and the method has important guiding significance on later preparation of sugar-containing monomers with different functions and research on the influence of isosaccharide in a two-arm sugar-containing polymer on the specific recognition effect of protein.

Description

technical field [0001] The present invention relates to the technical field of synthesis of double-armed sugar-containing compounds, in particular to a double-armed heterogeneous sugar-containing compound and a preparation method thereof. Background technique [0002] Click chemistry, also known as "link chemistry" and "dynamic combinatorial chemistry", is a form of splicing of small units under mild conditions to achieve molecular diversity construction with high selectivity. There are currently four types of click chemistry reactions in the field of organic synthesis: CuAAC reaction between terminal alkynes and azides; D-A reaction between alkenes; mercapto-ene reaction; and free radical-induced mercapto-alkyne reaction. Thiol-ene click chemistry can fully combine the advantages of photoinitiated processes with the advantages of traditional click reactions, with mild reaction conditions, high yields, high selectivity, biocompatibility and environmental friendliness, and ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/056C07H1/00
CPCC07H19/056C07H1/00
Inventor 叶飞刘美娜周志刘彩容孙佳郎周欣怡
Owner SHANGHAI INST OF TECH
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