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Modular synthesis of non-charged and ionic xylan carbamate derivatives from xylan carbonates
Carbohydrate Polymers ( IF 10.7 ) Pub Date : 2018-12-07 , DOI: 10.1016/j.carbpol.2018.12.012
Lars Gabriel , Martin Gericke , Thomas Heinze

Novel non-charged and ionic xylan carbamate (XC) derivatives were synthesized in a modular approach from xylan phenyl carbonate (XPC) as reactive intermediate. XPC with varying degrees of substitution (DS) from 0.5 to 1.9 were converted with different non-ionic primary and secondary amines in different molar ratio to obtain the corresponding XC with high conversion rates of up to 100%. In a similar way, ionic amines were employed for the aminolysis of XPC to obtain charged XC. The XC were characterized by NMR- and infrared spectroscopy. XPC proofed to be highly versatile building blocks for the preparation of ionic xylan derivatives. The type and amount of charged groups could be tuned efficiently. Moreover, high DS values of up to 1.4 for cationic- and 1.8 for anionic XC derivatives could be achieved, which is higher than reported previously for comparable ionic xylan derivatives that were prepared by “conventional” esterification and etherification reactions.



中文翻译:

由木聚糖碳酸酯模块化合成不带电和离子型木聚糖氨基甲酸酯衍生物

以木聚糖碳酸苯酯(XPC)为反应性中间体,以模块化的方式合成了新型的不带电荷的离子型木聚糖氨基甲酸酯(XC)衍生物。用不同摩尔比的不同非离子伯胺和仲胺将取代度(DS)在0.5至1.9之间的XPC转化为相应的XC,具有高达100%的高转化率。以类似的方式,将离子胺用于XPC的氨解以获得带电的XC。通过NMR和红外光谱对XC进行表征。XPC被证明是用于制备离子木聚糖衍生物的高度通用的构建基块。可以有效调整带电组的类型和数量。此外,阳离子XC衍生物的DS值最高可达1.4,阴离子XC衍生物的DS值最高可达1.8,

更新日期:2018-12-08
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