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

A click chemistry, mannose technology, applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of preparation process obstacles, single sugar unit structure, etc.

Active Publication Date: 2021-08-13
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the current studies only involve a click chemical reaction, and the structure of the sugar unit involved is relatively simple, which leads to obstacles in the preparation process of compounds containing multiple sugar unit structures.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Synthesis of Compound B

[0070] Compound A (1,3-bis(allyloxy)-2-((allyloxy)methyl)prop-2-yl) tert-butyl carbamate (0.3g, 0.8mmol) and mercaptomannose (α-Man-SH) (1.1g, 3.1mmol) was dissolved in 5mL of anhydrous dichloromethane solution, followed by the addition of 2,2-dimethoxy-2-acetophenone (DMPA) (22.5mg, 0.09mmol ). Irradiate with 365nm ultraviolet light at room temperature and stir for 45min. After TLC monitoring until the reaction is completed, the reaction solution was washed with dichloromethane (50mL×3) and saturated brine (50mL×3) respectively, and the organic phase collected after extraction was dried with anhydrous sodium sulfate, filtered, and distilled under reduced pressure After concentration and purification by column chromatography, 1.1 g of a light yellow viscous product was obtained, namely compound B, with a yield of 90%.

[0071] The H NMR spectrum and the C NMR spectrum of the obtained compound B can be found in figure 1 and figure 2 shown....

Embodiment 2

[0078] Synthesis of Compound D

[0079] Compound C (1,3-bis(allyloxy)-2-(((prop-2-yn-1-yloxy)methyl)prop-2-yl)carbamate tert-butyl ester (1.3g ,3.9mmol) and azidomannose (α-Man-N 3 ) (1.6g, 4.3mmol) dissolved in 20mL t-BuOH / H 2 O (1:1 v / v) mixed solution, then added sodium ascorbate (0.8g, 3.9mmol) and copper sulfate pentahydrate (0.5g, 2.0mmol), stirred at room temperature for 5h. After TLC monitoring until the end of the reaction, the reaction solution was washed with dichloromethane (50mL×3) and saturated brine (50mL×3) respectively, and the organic phase collected after extraction was dried with anhydrous sodium sulfate, filtered, and depressurized Concentrated by distillation and purified by column chromatography, 2.6 g of a light yellow viscous product was obtained with a yield of 94%.

[0080] The H NMR spectrum and the C NMR spectrum of the obtained compound D can be found in Figure 5 and Figure 6 shown.

[0081] 1 H NMR (500MHz, CDCl 3 ):δ=7.71(s,1H),5.98–5....

Embodiment 3

[0091] Synthesis of Compound G

[0092] Compound F (tert-butyl (1-(allyloxy)-3-(prop-2-yn-1-yloxy)-2-((prop-2-yn-1-yloxy)methyl propyl-2-yl) carbamate (0.5g, 1.5mmol) and azidomannose (α-Man-N 3 ) (1.2g, 3.1mmol) dissolved in 20mL t-BuOH / H 2 O (1:1 v / v) mixed solution, then added sodium ascorbate (0.3g, 1.5mmol) and copper sulfate pentahydrate (0.2g, 0.8mmol), stirred at room temperature for 5h. After TLC monitoring until the end of the reaction, the reaction solution was washed with dichloromethane (50mL×3) and saturated brine (50mL×3) respectively, and the organic phase collected after extraction was dried with anhydrous sodium sulfate, filtered, and depressurized Concentrated by distillation and purified by column chromatography, 1.5 g of a light yellow viscous product was obtained with a yield of 94%.

[0093] The H NMR spectrum and the C NMR spectrum of the prepared compound G are shown in Figure 11 and Figure 12 shown.

[0094] 1 H NMR (500MHz, CDCl 3 ):δ=7.72(...

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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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H1/00C07H15/14C07H19/056
CPCC07H1/00C07H15/14C07H19/056Y02P20/55
Inventor 刘美娜王梦彤叶飞周志杨文璐梁雯
Owner SHANGHAI INST OF TECH
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