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Norbornene derivative based homopolymer containing heterogeneous sugar units and synthetic method of homopolymer

A technology for norbornene and a synthesis method, which is applied in the field of sugar-containing polymer synthesis, can solve problems such as complex multi-step operations of block copolymerization, and achieve the effects of broadening synthesis routes, regular structure and mild reaction conditions.

Active Publication Date: 2018-12-14
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, block copolymerization often requires complex multi-step operations

Method used

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  • Norbornene derivative based homopolymer containing heterogeneous sugar units and synthetic method of homopolymer
  • Norbornene derivative based homopolymer containing heterogeneous sugar units and synthetic method of homopolymer
  • Norbornene derivative based homopolymer containing heterogeneous sugar units and synthetic method of homopolymer

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Embodiment 1

[0044] 1. Synthesis of norbornene dicarboxamide propylene glycol NB-2OH (1)

[0045] Take the three-neck round bottom bottle cooled after high temperature treatment, add norbornene dianhydride (5g, 30mmol) and aminomethylpropanediol (3.15g, 30mmol), and add 150mL of toluene. Connect the h-type water separator at the mouth of the bottle, connect the serpentine condenser above it, and reflux the reaction in an oil bath at 135°C for 16 hours. After the reaction, the toluene is distilled off under reduced pressure. Purify directly through a silica gel column to obtain 2.8 g of a white solid with a yield of 37%. 1 H NMR (500MHz, CDCl3 ):δ=1.17(s,3H),1.49(d,J=8.7Hz 1H),1.57(d,J=8.8Hz,1H),3.23(m,2H),3.40(m,2H),3.58– 3.68(m,4H),4.19(d,J=11.8,2H),6.15(s,2H).

[0046] 2. Synthesis of 2,2-diyne-norbornene dicarboxamide ethylene glycol NB-2Alkyne (2)

[0047] Add norbornenedicarboxamide propylene glycol (1.88g, 7.5mmol) into a dry single-necked round-bottomed reaction flask, then add 3...

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Abstract

The invention discloses a norbornene derivative based homopolymer containing heterogeneous sugar units and a synthetic method of the homopolymer. With the adoption of a gradient organic synthesis method, an acetyl protected norbornene monomer NB-Man-Glu-OAc containing heterogeneous sugars is prepared by combining with a copper catalyzed azido-terminal alkyne [3+2] cycloaddition reaction (CuAAC), then a linear sugar-containing homopolymer with controllable molecular weight and narrower molecular weight distribution is obtained with ROMP (ring-opening metathesis polymerization), and the final homopolymer PNB-Man-Glu-OH containing the heterogeneous sugar units is obtained by deprotection. One simple and efficient path is provided for synthesis of sugar-containing polymers which contain the heterogeneous sugar units, and synthesis of the sugar-containing polymers has great guiding significance in studying special recognition mechanism for the sugar units and lectin and developing functional sugar-containing polymers with special biological diagnosis functions.

Description

technical field [0001] The invention relates to the technical field of synthesis of sugar-containing polymers, in particular to a norbornene derivative homopolymer containing heterogeneous sugar units and a synthesis method thereof. Background technique [0002] Sugar-containing polymers refer to functional polymer materials formed by introducing sugar units into polymer molecular chains through different chemical reaction pathways. Since glycopolymers have the same "sugar cluster effect" as natural polysaccharides, glycopolymers are endowed with biological functionality with high affinity for specific proteins. In the application of glycopolymers in clinical diagnosis, the specific recognition of glycounits and lectins plays a key role. However, most of the reported glycopolymers contain only a single saccharide unit, often ignoring the potential synergistic effect of heterogeneous saccharide units in the polymer backbone. The regularity of structurally ordered sugar-cont...

Claims

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Application Information

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IPC IPC(8): C08F132/08C08F8/00
CPCC08F8/00C08F132/08
Inventor 朱玉刘美娜叶文玲邓维苗登云刘志峰陶朝富
Owner SHANGHAI INST OF TECH
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