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Preparation method of glycosyl and polypeptide modified 1, 2, 3-triazole compound

A technology for the modification of triazole compounds and polypeptides, which is applied in the field of combining organic synthesis and chemical biology, can solve the problems of harsh reaction conditions and narrow substrate range, and achieve the effect of simple operation and high potential application value

Active Publication Date: 2021-06-15
RENMIN UNIVERSITY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few methods for synthesizing such compounds, and the substrate range is narrow, the reaction conditions are harsh, and most of them require the participation of transition metals.

Method used

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  • Preparation method of glycosyl and polypeptide modified 1, 2, 3-triazole compound
  • Preparation method of glycosyl and polypeptide modified 1, 2, 3-triazole compound
  • Preparation method of glycosyl and polypeptide modified 1, 2, 3-triazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The preparation of the compound shown in embodiment 1, formula Ⅰ-1

[0045]

[0046] Under air conditions, add trifluoromethyl-substituted acetonylidene-protected fructose (Formula 1) (0.2mmol), DABCO (0.4mmol), NaN 3 (0.8mmol), tetrahydropyrrole (Formula 3) (0.6mmol) and tetrahydrofuran (1.0mL). It was heated freely to 50°C and reacted for 12 hours. After the reaction was completed, 20 mL of ethyl acetate and 3.0 mL of 0.5 M dilute hydrochloric acid were added for extraction and separation, and the organic phase was washed with 3.0 mL of saturated brine, then dried, rotary evaporated, and subjected to column chromatography. After weighing, 46 mg of the compound represented by formula I-1 was isolated with a yield of 54%.

[0047] figure 1 Formula I-1 (((3aR,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolane) prepared for this example [4,5-b:4',5'-d]pyran-3a-yl)methyl 5-(pyrrolidin-1-yl)-1H-1,2,3-triazole-4-carboxylic acid The proton nuclear magne...

Embodiment 2

[0049] The preparation of the compound shown in embodiment 2, formula Ⅰ-2

[0050]

[0051]

[0052] Under air conditions, add trifluoromethyl-substituted acetonide-protected glucose (Formula 1) (0.2mmol), DABCO (0.4mmol), TMSN to the reaction tube in sequence 3 (0.8mmol), tetrahydropyrrole (Formula 3) (0.6mmol) and tetrahydrofuran (1.0mL). It was heated freely to 50°C and reacted for 12 hours. After the reaction was completed, 20 mL of ethyl acetate and 3.0 mL of 0.5 M dilute hydrochloric acid were added for extraction and separation, and the organic phase was washed with 3.0 mL of saturated brine, dried, rotary evaporated, and subjected to column chromatography. After weighing, 52 mg of the compound represented by formula I-2 was isolated, with a yield of 61%.

[0053] figure 2 (3aR,5R)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuran prepared for the examples of the present invention 1H NMR Spectrum of [2,3-d][1,3]dioxo-6-yl 5-(pyrrolidin-1-yl)-1H...

Embodiment 3

[0055] The preparation of the compound shown in embodiment 3, formula Ⅰ-3

[0056]

[0057] Under air conditions, add trifluoromethyl-substituted acetonide-protected glucose (Formula 1) (0.2mmol), DABCO (0.4mmol), NaN 3 (0.8 mmol), proline methyl ester (Formula 3) (0.6 mmol) and tetrahydrofuran (1.0 mL). It was heated freely to 80°C and reacted for 12 hours. After the reaction was completed, 20 mL of ethyl acetate and 3.0 mL of 0.5 M dilute hydrochloric acid were added for extraction and separation, and the organic phase was washed with 3.0 mL of saturated brine, dried, rotary evaporated, and subjected to column chromatography. After weighing, 58 mg of the compound represented by formula I-3 was isolated, with a yield of 60%.

[0058] image 3 (3aR,5R)-5-((R)-2,2-dimethyl-1,3dioxolan-4-yl)-2,2-dimethyltetrahydrofuranyl 5 -((S)-2-(methoxycarbonyl)pyrrolidin-1-yl)-1H-1,2,3-triazole-4-carboxylate proton nuclear magnetic resonance spectrum, characterized as follows:

[005...

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Abstract

The invention discloses a preparation method of a glycosyl and polypeptide modified 1, 2, 3-triazole compound. The preparation method of the 1, 2, 3-triazole compound comprises the following steps (1) or (2): (1) under the catalysis of triethylene diamine, reacting a compound as shown in a formula 1 or a formula 1 ', a compound as shown in a formula 2 and a compound as shown in a formula 3 or peptide to obtain the 1, 2, 3-triazole compound as shown in a formula I or a formula I '; and 2) under the catalysis of the triethylene diamine, reacting the compound as shown in the formula 1 or the formula 1'and the compound as shown in the formula 2 with the peptide to obtain the 1, 2, 3-triazole compound as shown in the formula II or the formula II '. The preparation method provided by the invention overcomes the defects of narrow substrate range, tedious synthesis steps, harsh reaction conditions, participation of a transition metal catalyst and the like in the existing method, has the advantages of cheap and easily available raw materials, simple operation, no need of anhydrous and anaerobic operation, and smooth operation under the air condition, and has very high value in the fields of synthetic chemistry and chemical biology.

Description

technical field [0001] The invention relates to a preparation method of glycosyl and polypeptide modified 1,2,3-triazole compounds, which belongs to the technical field of combining organic synthesis and chemical biology. Background technique [0002] 1,2,3-Triazole compounds are an important class of five-membered nitrogen-containing heterocyclic skeletons, which are widely used in biochemistry and medicinal chemistry. The modification of the triazole skeleton has become an important method for the preparation of medicines, pesticides and insecticides. For example, the introduction of sugar groups and polypeptides into the triazole parent structure will have a significant impact on its biological activity, environmental adaptability and pharmacological properties. At present, there are few methods for synthesizing such compounds, and the scope of substrates is narrow, the reaction conditions are harsh and most of them require the participation of transition metals. Theref...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H1/00C07H13/10C07K5/062C07K1/107
CPCC07H13/10C07H1/00C07K5/06026Y02P20/55
Inventor 吕雷阳李志平
Owner RENMIN UNIVERSITY OF CHINA