Three-arm mannose derivative and preparation method thereof through combination with double-click chemistry

Abstract

The invention relates to a three-arm mannose derivative and a preparation method thereof through combination with double-click chemistry. Firstly, a three-arm terminal alkene / alkyne compound and [alpha]-D-azide mannose ([alpha]-Man-N3) are used for carrying out a CuAAC reaction between end group alkyne and azide to generate a rigid triazole group; then, the rigid triazole group and [alpha]-D-sulfydryl mannose ([alpha]-Man-SH) carry out a Thiol-ene reaction between end group alkene and the sulfydryl to generate a flexible thioether bond; and then, under an acidic condition of trifluoroacetic acid, protection of t-butyloxycarboryl is removed to obtain one series of three-arm mannose derivatives. Compared with the prior art, the invention utilizes the advantages of the click chemistry reaction to innovatively synthesize three kinds of three-arm mannose derivatives with different structures so as to be favorable for jointly utilizing RAFT polymerization in the later stage to prepare a sugar-containing polymer of which the side chain contains tri-functional mannose and perform an important guidance meaning for researching the influence of the rigidity and the flexibility of different branched chains of the polymer of which the side chain contains three-arm mannose for the biological characteristics.

Description

technical field

[0001] The invention relates to the technical field of synthesis of three-armed mannose derivatives, in particular to a preparation method of three-armed mannose derivatives and double-click chemistry. Background technique

[0002] Natural polysaccharides participate in a series of complex biological processes of living organisms, and play an irreplaceable role, including cell recognition, cell proliferation, signal transmission, and pathogen infection. Therefore, people are very interested in the synthesis of sugar polymers with controllable structures. interest. Glycopolymers (glycopolymers) are a class of synthetic macromolecules containing sugar groups, which have good water solubility, biological antifouling, molecular recognition, and good "sugar clustering effect". With the rapid development of polymer synthesis chemistry, especially the synthesis technology of functional sugar polymers, some strategies of controlled free radical polymerization and cl...

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