Method for preparing mannose-containing derivatives capable of being used for post-polymerization modification through double-click chemistry combination

A click chemistry and post-polymerization technology, applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., to achieve the effects of improving the preparation method, simple experimental operation, and stable synthesis method

Active Publication Date: 2021-04-02
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, most of the existing mannose derivatives are prepared by a single CuAAC reaction, and their structures are simple and mostly irreversible rigid structures

Method used

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  • Method for preparing mannose-containing derivatives capable of being used for post-polymerization modification through double-click chemistry combination
  • Method for preparing mannose-containing derivatives capable of being used for post-polymerization modification through double-click chemistry combination
  • Method for preparing mannose-containing derivatives capable of being used for post-polymerization modification through double-click chemistry combination

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] (1) Preparation of compound 1

[0060] Take 5-norbornene-2,3-dicarboxylic anhydride (5.00g, 30.46mmol) and 2-amino-2-methyl-1,3-propanediol (3.80g, 36.14mmol) into a 250ml dry reaction flask In, nitrogen was introduced for 10 minutes, then 150ml of anhydrous toluene was added, refluxed at 120°C for 16 hours and a water separator was installed. After the completion of the reaction was confirmed by thin-layer chromatography, the solvent was removed by rotary evaporation, and the product was separated by silica gel column chromatography to obtain 5.21 g of a white solid with a yield of 68%.

[0061] 1 H NMR (500MHz, CDCl 3 )δ=6.15(s,2H),4.19(d,J=12.0Hz,2H),3.58-3.68(m,4H),3.40(m,2H),3.23(m,2H),1.57(d,J =9.0Hz, 1H), 1.49(d, J=8.5Hz 1H), 1.17(s, 3H). 13 C NMR (125MHz, CDCl 3 )δ=178.72,165.49,134.53,131.12,128.16,79.43,77.32,77.07,76.82,74.58,70.31,64.84,62.25,58.31,51.79,45.41,19.34. 13 h 17 NO 4 H(M+H + )calc.for:252.11576;found:252.11394.

[0062] (2) Preparation...

Embodiment 2

[0071] (4) Compound G 1 preparation of

[0072]Dissolve compound 3 (1.80g, 5.24mmol) and 1-pentanethiol (0.74ml, 5.86mmol) in 20ml of anhydrous CH 2 Cl 2 , after stirring for 30 min, a dichloromethane solution of dimethylphenylphosphine (3.50ml, 7mmol%) was added (the concentration of dimethylphenylphosphine was 0.1M in CH 2 Cl 2 : Dissolve 142 μL of pure dimethylphosphorus in 10 mL of CH 2 Cl 2 prepared in). After reacting at room temperature for 3 h, thin layer chromatography confirmed whether the reaction was complete. After the reaction was completed, it was extracted with saturated brine and dichloromethane, dried with anhydrous sodium sulfate, and the product was separated by silica gel column chromatography to obtain 2.43 g of light yellow oily liquid (i.e. compound G 1 ), the yield is 98%.

[0073] The obtained compound G 1 The hydrogen NMR spectrum and the carbon NMR spectrum can be found in Figure 5 with Image 6 .

[0074] 1 H NMR (500MHz, CDCl 3 )δ6....

Embodiment 3

[0080] (6) Compound G 2 preparation of

[0081] Dissolve compound 3 (2.00g, 5.83mmol) and 3-mercapto-1-propanol (0.61ml, 7.06mmol) in 20ml of anhydrous CH 2 Cl 2 After stirring for 30 min, dimethylphenylphosphine (0.1M in CH 2 Cl 2 , 4.10ml, 7mol%) to continue the reaction, after 3h at room temperature, thin-layer chromatography confirmed whether the reaction was complete. After the reaction was completed, it was extracted with saturated brine and dichloromethane, and after drying with anhydrous sodium sulfate, the product was separated by silica gel column chromatography to obtain 2.53 g of light yellow oily liquid (i.e. compound G 2 ), the yield is 95%.

[0082] The obtained compound G 2 The H NMR spectrum and C NMR spectrum can be found in Figure 7 with Figure 8 shown.

[0083] 1 H NMR (500MHz, CDCl 3 )δ6.09(s, 2H), 4.58(d, J=11.5Hz, 1H), 4.35(d, J=11.5Hz, 1H), 4.08(t, J=2.0Hz, 2H), 3.92(d, J=9.0Hz, 1H), 3.79(d, J=9.0Hz, 1H), 3.70(t, J=6.0Hz, 2H), 3.32(s, 2H),...

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Abstract

The invention relates to a method for preparing mannose-containing derivatives capable of being used for post-polymerization modification by double-click chemistry combination. The method comprises the following steps: under the actions of propargyl bromide and acryloyl chloride respectively, preparing a compound with terminal alkyne and terminal olefin by using a Williessen ether-forming reaction; and then performing sulfydryl-alkene addition reaction on terminal olefin and sulfydryl compounds, and performing CuAAC reaction on terminal alkyne and acetyl-protected alpha-D-pyranomannose azide.Compared with the prior art, mercaptan substances with different structures are successfully combined with the alpha-D-pyranomannose azide through a mercapto-alkene addition reaction and GuAAC combined method for the first time, the mannose-containing derivative capable of being applied to post-polymerization modification is prepared, and the synthesis method is stable, efficient and high in yield. A considerable way is provided for obtaining a sugar-containing homopolymer with controllable molecular weight and narrower molecular weight distribution in the later period.

Description

technical field [0001] The invention belongs to the technical field of synthesis of sugar-containing derivatives, and relates to a method for preparing mannose-containing derivatives that can be used for post-polymerization modification through double-click chemistry combination. Background technique [0002] Glycopolymers are polymers with a non-carbohydrate backbone but with side chains or terminal carbohydrates, usually prepared by stepwise growth condensation reactions or ring-opening polymerization. The polymer is highly hydrophilic and can selectively interact with a variety of biomolecules, such as transporters (GLUTs), proteins (lectins), enzymes (such as β-glucuronidase), and other substances. Glycopolymer-mediated interactions mainly involve the specific recognition of sugar-binding protein (GBP), which facilitates the study of sugar-protein interactions, which play an indispensable role in a series of complex biological processes. Functions: such as intercellular...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H1/00C07H19/056
CPCC07H1/00C07H19/056Y02P20/55
Inventor 王梦彤刘美娜刘志峰周志叶飞梁雯赵美玲
Owner SHANGHAI INST OF TECH
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