Solid Phase Stepwise Synthesis of Polyethylene Glycols.
Solid Phase Stepwise Synthesis of Polyethylene Glycols.
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DOI：
10.1002/chem.201703004
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发表时间：
2017-10-26
期刊：
影响因子：
--
通讯作者：
Fang S
中科院分区：
文献类型：
--
作者：
Khanal A;Fang S
以聚苯乙烯为载体，通过四甘醇单体的分步加成反应合成了聚乙二醇及其衍生物。单体的一端含有甲苯磺酰基，另一端含有二甲氧基三苯甲基。使用含有4-苄氧基苄醇官能团的Wang树脂作为载体。合成循环包括去质子化、威廉姆森醚形成（偶联）和去三苯甲基化。用三氟乙酸实现PEG从固体支持物的裂解。包括单体合成在内的合成完全不需要色谱法。以高产率获得了包括在两个末端具有不同官能度的PEG产物。用ESI和MALDI-TOF MS分析产物，发现其接近单分散性。通过在聚苯乙烯载体上逐步添加单体，可以容易地获得纯PEG和衍生物。包括单体合成在内的整个合成过程均不使用色谱法。在固体载体上的反应是定量的。可以避免解聚副反应或将其保持在最低限度。
Polyethylene glycol (PEG) and derivatives with eight and twelve ethylene glycol units were synthesized by stepwise addition of tetraethylene glycol monomers on a polystyrene solid support. The monomer contains a tosyl group at one end and a dimethoxytrityl group at the other. The Wang resin, which contains the 4-benzyloxy benzyl alcohol function, was used as the support. The synthetic cycle consists of deprotonation, Williamson ether formation (coupling), and detritylation. Cleavage of PEGs from solid support was achieved with trifluoroacetic acid. The synthesis including monomer synthesis was entirely chromatography-free. PEG products including those with different functionalities at the two terminals were obtained in high yields. The products were analyzed with ESI and MALDI-TOF MS and were found close to monodispersity. Pure PEGs and derivatives are readily accessible via stepwise addition of monomers on a polystyrene support. The entire synthesis including monomer synthesis is chromatography-free. Reactions on solid support are quantitative. The depolymerization side reaction can be avoided or kept at minimum.
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影响因子：
3.6
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