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Method for synthesizing sugary derivative used for post polymerization modification by double-click chemical combination

A click chemistry and post-polymerization technology, which is applied in the direction of sugar derivatives, sugar derivatives, sugar derivatives preparation, etc., can solve the problems of side chain functional group polymerization introduction and polymerization reaction out of control, etc., to achieve molecular weight controllable, narrow The effect of molecular weight distribution and simple operation

Active Publication Date: 2019-11-05
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still a large number of side chain functional groups that cannot be directly polymerized by any existing controllable polymerization technology. These functional groups may completely prevent controlled polymerization, or may participate in side reactions that lead to runaway polymerization reactions.

Method used

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  • Method for synthesizing sugary derivative used for post polymerization modification by double-click chemical combination
  • Method for synthesizing sugary derivative used for post polymerization modification by double-click chemical combination
  • Method for synthesizing sugary derivative used for post polymerization modification by double-click chemical combination

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] 1. Synthesis of Compound 1

[0070] Weigh aminomethylpropanediol (AMPD) (10.00g, 95.11mmol) and dissolve in 125mL (MeOH:THF=4:1) solvent, add di-tert-butyl dicarbonate (Diboc ) (31.14g, 142.67mmol), sodium bicarbonate (15.98g, 190.22mmol) was added under stirring, stirred evenly, and then reacted at room temperature for 12h, followed by TLC detection. After the reaction was completed, it was washed with ethyl acetate / water, the organic phase was dried with anhydrous sodium sulfate, and then silica gel powder was added to directly spin dry the sample. Silica gel column chromatography (developing agent: PE / EA (v / v)=1:1, Eluent: PE / EA (v / v)=2:1) ​​19.50 g of white powdery solid (compound 1) was isolated with a yield of 92%. 1 H NMR (500MHz, CDCl 3 )δ=5.10(s,1H),3.71(dd,J=11.1,3.7Hz,2H),3.59(dd,J=11.2,6.6Hz,2H),1.41(s,9H),1.15(s,3H ).

[0071] 2. Synthesis of Compound 2

[0072] Weigh compound 1 (10.00g, 48.70mmol) and dissolve it in 50mL N,N-dimethylformamide, put it ...

Embodiment 2

[0080] 1. The synthesis of compound 1-compound 3 and compound Boc-AMP-Glu-ene is as in Example 1.

[0081] 2. Synthesis of compound Boc-AMP-Glu-Gal

[0082] In the same synthesis method as Boc-AMP-Glu-Glu, the compound Boc-AMP-Glu-ene reacts with β-D-galactose sulfhydryl compound (Gal-SH) to prepare Boc-AMP-Glu-Gal, and obtains a colorless viscous material, yield 77%. The hydrogen and carbon spectra of Boc-AMP-Glu-Gal are as follows Figure 5 and Figure 6 shown. 1 H NMR (500MHz, CDCl 3 )δ=7.76(d, J=1.9Hz, 1H), 5.87(d, J=8.8Hz, 1H), 5.41(dt, J=12.1, 6.6Hz, 3H), 5.21(dt, J=16.2, 9.8 Hz, 2H), 5.03(dd, J=10.0, 3.3Hz, 1H), 4.93(s, 1H), 4.62(d, J=3.6Hz, 2H), 4.49(dd, J=10.0, 2.4Hz, 1H ),4.29(dd,J=12.6,4.9Hz,1H),4.15–4.06(m,3H),4.03–3.99(m,1H),3.94(t,J=6.6Hz,1H),3.60(dd, J=8.9, 4.3Hz, 1H), 3.50(ddd, J=12.7, 8.9, 4.2Hz, 4H), 3.40(d, J=8.5Hz, 1H), 2.72(ddd, J=17.4, 12.5, 5.6Hz ,2H),2.13(s,3H),2.08–2.03(m,9H),2.01(d,J=4.9Hz,6H),1.96(s,3H),1.85(s,3H),1.39(s, 9H), 1.28(d, J=2.8H...

Embodiment 3

[0084] 1. The synthesis of compound 1-compound 3 and compound Boc-AMP-Glu-ene is as in Example 1.

[0085] 2. Synthesis of compound Boc-AMP-Glu-Man

[0086] In the same synthesis method as Boc-AMP-Glu-Glu, the compound Boc-AMP-Glu-ene reacts with α-D-mannose sulfhydryl compound (Man-SH) to prepare Boc-AMP-Glu-Man, and obtains a colorless viscous material, yield 77%. The hydrogen and carbon spectra of Boc-AMP-Glu-Man are as follows Figure 7 and Figure 8 shown. 1 H NMR (500MHz, CDCl 3)δ=7.75(s,1H),5.87(d,J=8.8Hz,1H),5.46–5.40(m,2H),5.33–5.30(m,1H),5.27(d,J=9.8Hz,1H ),5.22(dd,J=10.6,7.1Hz,3H),4.89(s,1H),4.61(d,J=4.6Hz,2H),4.38–4.32(m,1H),4.32–4.27(m, 2H), 4.16–4.05(m, 4H), 4.03–3.99(m, 1H), 3.59(d, J=9.0Hz, 1H), 3.48–3.46(m, 2H), 3.40(d, J=6.6Hz ,1H),2.75–2.61(m,2H),2.14(s,3H),2.02(dd,J=12.8,7.1Hz,15H),1.97(s,3H),1.85(s,3H),1.39( s,9H),1.28(d,J=3.3Hz,3H). 13 C NMR (125MHz, CDCl 3 )δ=170.32,170.23,169.77,169.67,169.61,169.53,169.23,168.68,145.54,145.47,121.01,120.96,85...

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Abstract

The invention relates to a method for synthesizing a sugary derivative used for post polymerization modification by double-click chemical combination. The method comprises the steps: firstly, carryingout a reaction of di-tert-butyl dicarbonate (Diboc) with aminomethyl propanediol (AMPD), protecting an amino group in AMPD with tert-butoxycarbonyl, and then introducing terminal alkyne and terminalolefin at the tail end of the compound by a Williamson etherification reaction; and then carrying out CuAAC reaction on terminal alkyne with acetyl-protected azido sugar (R-N3). Compared with the prior art, the method combines the advantages of CuAAC and Thiol-ene click chemistry, provides a simple and fast way for synthesis of active functional groups which can be subjected to post polymerizationmodification, and has important guiding significance for synthesis of the sugary polymer with controllable molecular weight, narrow molecular weight distribution and biological function.

Description

technical field [0001] The invention relates to a method for synthesizing sugar-containing derivatives, in particular to a method for synthesizing sugar-containing derivatives that can be used for post-polymerization modification by double-click chemistry. Background technique [0002] The function of glycopolymers is similar to that of some natural glycoconjugates, and can imitate or even surpass the performance of natural glycoconjugates in some specific recognition. Since the pioneering work of Horejsi et al. on the specific precipitation of glycopolymers and lectins, the design and synthesis of functional glycopolymer materials has become a very important topic in the fields of chemistry, biology and medicine. Its research focuses on its special structure. The structure of sugar-containing polymers mainly includes polymer backbones and sugar-containing moieties linked by covalent bonds. Synthesis of sugar-containing polymers with different structures and components is a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/056C07H1/00
CPCC07H19/056C07H1/00Y02P20/55
Inventor 王星又刘美娜苗登云刘志峰
Owner SHANGHAI INST OF TECH
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