Preparative Chiral Liquid Chromatography for Enantiomeric Separation of Pheromones

Christopher I. Keeling; Hien T. Ngo; Kathryn D. Benusic; Keith N. Slessor

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Preparative Chiral Liquid Chromatography for Enantiomeric Separation of Pheromones

机译：制备的手性液相色谱分离对映体。

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摘要

Cellulose triacetate was investigated as a chiral stationary phase for preparatively separating the enantiomers of lineatin, frontalin, exo-brevicomin, endo-brevicomin, verbenone, (E)-conophthorin, and grandisol. Tens of milligrams of both enantiomers were efficiently prepared in high percentage enantiomeric excess from one injection of each compound except grandisol. We prepared grandisyl acetate, benzoate, and 4-bromobenzoate to determine if derivatization of the free alcohol might improve separation. Of these, grandisyl 4-bromobenzoate provided the best separation but was still not very well resolved. Preparative separation of enantiomers on cellulose triacetate is a viable alternative to stereoselective synthesis when semiochemicals of very high enantiomeric purity are required for biological testing.

机译：研究了三乙酸纤维素作为手性固定相的方法，该方法用于制备可乐宁，额叶素，exo-brevicomin，endo-brevicomin，马鞭酮，（E）-conophthorin和Grandisol的对映异构体。通过从大丁酚以外的每种化合物的一次注射中，以高百分比的对映体过量有效地制备了数十毫克的两种对映体。我们准备了乙酸大丁酯，苯甲酸酯和4-溴苯甲酸酯，以确定游离醇的衍生化是否可以改善分离。其中，4-溴苯甲酸大丁烷基酯提供了最好的分离效果，但分离度仍然不是很好。当生物学测试需要非常高对映异构纯度的半化学化合物时，在三乙酸纤维素上对映异构体的制备分离是立体选择合成的可行替代方法。

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来源
《Journal of Chemical Ecology》 |2001年第3期|487-497|共11页
作者
Christopher I. Keeling; Hien T. Ngo; Kathryn D. Benusic; Keith N. Slessor;
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作者单位

Department of Chemistry Simon Fraser University;

Department of Chemistry Simon Fraser University;

Department of Chemistry Simon Fraser University;

Department of Chemistry Simon Fraser University;

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正文语种 eng
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关键词
Cellulose triacetate; preparative chiral liquid chromatography; lineatin; frontalin; exo-brevicomin; endo-brevicomin; verbenone; (E)-conophthorin; grandisol;

机译：三乙酸纤维素;制备型手性液相色谱法;可乐宁;额叶蛋白;外-brevicomin;内-brevicomin;马洛酮;（E）-香豆素;大戟醇;

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机译：基于多糖的手性固定相的液相色谱法制备新的选择性CB_2受体激动剂的对映体分离：X射线结构分析确定对映体纯度和绝对立体化学分配
2. Simultaneous separation of coplanar and chiral polychlorinated biphenyls by off-line pyrenyl-silica liquid chromatography and gas chromatography. Enantiomeric ratios of chiral congeners [J] . Ramos L., Gonzalez MJ., Hernandez LM. Analytical chemistry . 1999,第1期

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3. Enantiomeric separations of alpha-aryl ketones with cyclofructan chiral stationary phases via high performance liquid chromatography and supercritical fluid chromatography [J] . Breitbach Anthony S., Lim Yeeun, Xu Qing-Long, Journal of chromatography, A: Including electrophoresis and other separation methods . 2016,第Null期

机译：高效液相色谱和超临界液相色谱法与环果聚糖手性固定相分离α-芳基酮的对映体
4. Chromatographic chiral separation on chiral stationary phase by HPLC: Cellulose 4-methylbenzoate beads as chiral stationary phase for chiral separation of some racemates by high performance liquid chromatography [C] . Han Xiaoqian, Zhang Dabing, Liu Wanliang, 2011 International Conference on Consumer Electronics, Communications and Networks . 2011

机译：HPLC在手性固定相上进行色谱手性分离：以4-甲基苯甲酸纤维素微珠为手性固定相，通过高效液相色谱手性分离某些外消旋体
5. Enantiomeric separations on cyclodextrin-based and synthetic polymeric chiral stationary phases by high performance liquid chromatography and supercritical fluid chromatography [D] . Han, Xinxin 2007

机译：高效液相色谱和超临界流体色谱法在基于环糊精和合成聚合物手性固定相上的对映体分离
6. Optimizing Column Length and Particle Size in Preparative Batch Chromatography Using Enantiomeric Separations of Omeprazole and Etiracetam as Models: Feasibility of Taguchi Empirical Optimization [O] . Jörgen Samuelsson, Marek Leśko, Martin Enmark, -1

机译：以奥美拉唑和依替西坦的对映体分离为模型在分批制备色谱中优化柱长和粒径：田口实证优化的可行性
7. Enantiomeric separations on cyclodextrin-based and synthetic polymeric chiral stationary phases by high performance liquid chromatography and supercritical fluid chromatography [O] . Han, Xinxin 2007

机译：高效液相色谱和超临界流体色谱法在基于环糊精和合成聚合物手性固定相上的对映体分离

Preparative Chiral Liquid Chromatography for Enantiomeric Separation of Pheromones

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