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
CN112592376AActive Publication Date: 2021-04-02SHANGHAI INST OF TECH
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
SHANGHAI INST OF TECH
Publication Date
2021-04-02

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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.
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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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