A method for the preparation of mannose-containing derivatives that can be used for post-polymerization modification by double click chemistry

A technology of click chemistry and post-polymerization, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., to achieve the effect of stable synthesis methods

Active Publication Date: 2022-07-08
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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  • A method for the preparation of mannose-containing derivatives that can be used for post-polymerization modification by double click chemistry
  • A method for the preparation of mannose-containing derivatives that can be used for post-polymerization modification by double click chemistry
  • A method for the preparation of mannose-containing derivatives that can be used for post-polymerization modification by double click chemistry

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] (1) Preparation of compound 1

[0062] 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 the medium, nitrogen was introduced for 10min, then 150ml of anhydrous toluene was added, refluxed at 120°C for 16h, 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%.

[0063] 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.HRMS(ESI):C 13 H 17 NO 4 H(M+H + )calc.for:252.11576;found:...

Embodiment 2

[0073](4) Compound G 1 preparation

[0074] Compound 3 (1.80 g, 5.24 mmol) and 1-pentanethiol (0.74 ml, 5.86 mmol) were dissolved in 20 ml of anhydrous CH 2 Cl 2 After stirring for 30 min, a solution of dimethyl phenyl phosphorus in dichloromethane (3.50 ml, 7 mmol%) was added (the concentration of dimethyl phenyl phosphorus was 0.1 M in CH 2 Cl 2 : Dissolve 142 μL of pure dimethyl phosphorus in 10 mL of CH 2 Cl 2 prepared in). After 3 hours of reaction 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, dried with anhydrous sodium sulfate, and the product was separated by silica gel column chromatography to obtain 2.43 g of a pale yellow oily liquid (that is, compound G). 1 ) with a yield of 98%.

[0075] The prepared compound G 1 The H NMR spectrum and C NMR spectrum of , see Figure 5 and Image 6 .

[0076] 1 H NMR (500MHz, CDCl ...

Embodiment 3

[0082] (6) Compound G 2 preparation

[0083] Compound 3 (2.00 g, 5.83 mmol) and 3-mercapto-1-propanol (0.61 ml, 7.06 mmol) were dissolved in 20 ml of anhydrous CH 2 Cl 2 After stirring for 30 min, dimethylphenylphosphine (0.1 M in CH 2 Cl 2 , 4.10ml, 7mol%) to continue the reaction, after 3h reaction at room temperature, thin layer chromatography confirms whether the reaction is 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 2.53 g of pale yellow oily liquid (that is, compound G). 2 ) in 95% yield.

[0084] The prepared compound G 2 The H NMR and C NMR spectra of Figure 7 and Figure 8 shown.

[0085] 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), 3.19–3.08(m, 2...

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Abstract

The invention relates to a method for preparing a mannose-containing derivative that can be used for post-polymerization modification by combining double click chemistry. First, under the action of propargyl bromide and acryloyl chloride, respectively, a Williamson-forming ether is used to prepare a mannose-containing derivative. Compounds with terminal alkynes and terminal alkenes. Then, the terminal alkene and the mercapto compound undergo a mercapto-ene addition reaction, and the terminal alkyne and the acetyl-protected α-D-mannopyranosyl azide undergo a CuAAC reaction. Compared with the prior art, the present invention successfully combines thiol substances of different structures with α-D-mannopyranosyl azide through the combined method of mercapto-ene addition reaction and GuAAC to prepare A mannose-containing derivative that can be used for post-polymerization modification is developed. The synthesis method is stable and efficient, and provides a considerable way for obtaining sugar-containing homopolymers with controllable molecular weight and narrow molecular weight distribution in the later stage.

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 by combining double-click chemistry. Background technique [0002] Saccharide-containing polymers are polymers with a non-carbohydrate backbone, but with side chains or terminals containing carbohydrates, usually prepared by step-growth condensation reactions or ring-opening polymerization. The polymers are highly hydrophilic and can selectively interact with a variety of biomolecules, such as transporters (GLUTs), proteins (lectins), enzymes (such as β-glucuronidase), and others. The interactions mediated by sugar-containing polymers mainly involve the specific recognition of sugar-binding proteins (GBPs), which is beneficial to the study of sugar-protein interactions and plays an indispensable role in a series of complex biological processe...

Claims

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Application Information

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Patent Type & Authority Patents(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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