高效液相色谱法手性色谱柱分离3-羟基丁酸乙酯对映体
Separation of Enantiomers of Ethyl 3-Hydroxybutyrate by HPLC with Chiral Chromatographic Column
摘 要
采用Chiralcel OD-H手性色谱柱(4.6 mm× 250 mm,5 μm)作为分离柱,用高效液相色谱法对3-羟基丁酸乙酯对映体进行了拆分。在优化的色谱条件下,正己烷-异丙醇(100+5)溶液为流动相,流量为1.0 mL·min-1,柱温为25 ℃。3-羟基丁酸乙酯对映异构体在11 min内成功分离,分离度达4.25。
对映体
手性分离
3-羟基丁酸乙酯
HPLC
Enantiomers
Chiral separation
Ethyl 3-hydroxybutyrate
Abstract
A method of HPLC was proposed for the resolution of enantiomers of ethyl 3-hydroxybutyrate using Chiralcel OD-H chiral column (4.6 mm×250 mm, 5 μm) for separation. A mixture of n-hexane and isopropyl alcohol (100+5) was used as mobile phase with flow-rate of 1.0 mL·min-1. Column temperature of 25 ℃ was chosen. Under the optimized conditions, enantiomers of ethyl 3-hydroxybutyrate were successfully separated within 11 min, with resolution of 4.25.
中图分类号 O652.63
所属栏目 工作简报
基金项目 广西科学基金资助项目(2010GXNSFD 013020)
收稿日期 2013/2/21
修改稿日期
网络出版日期
作者单位点击查看
联系人作者向忠权(w66c6@sina.com)
备注向忠权(1984-),男,贵州贞丰人,硕士研究生,研究方向为手性药物的不对称催化合成。
引用该论文: XIANG Zhong-quan,WEI Zhi-ming,CHEN Xiao-peng,PU Guo-rong,SUN Guo-song. Separation of Enantiomers of Ethyl 3-Hydroxybutyrate by HPLC with Chiral Chromatographic Column[J]. Physical Testing and Chemical Analysis part B:Chemical Analysis, 2014, 50(2): 214～216
向忠权,韦志明,陈小鹏,蒲国荣,孙果宋. 高效液相色谱法手性色谱柱分离3-羟基丁酸乙酯对映体[J]. 理化检验－化学分册, 2014, 50(2): 214～216
被引情况:
【1】林桂就,韦志明,黄平,许朝芳,张丽娟,李致宝, "气相色谱法测定不对称合成手性4-苯基-2-丁醇反应液中的3种组分",理化检验－化学分册 52, 1456-1458(2016)
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参考文献
【1】王彦飞,马沛生,王加宁,等.脱水法合成3-羟基丁酸乙酯［J］.化学工业与工程, 2004,20(6):333-336.
【2】厦门大学.一种高对映体纯松叶蜂性信息素与立体异构体的合成方法:中国,CN102167666A［P］. 2011-08-31.
【3】HATANAKA M, NITTA H. Synthetic studies on thienamycin and 1β-methylcarbapenem starting from (R)-3-hydroxybutyrate［J］. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 1986,28:542-549.
【4】WANG Guang-wei, YING Nin, NEGISHI E. Highly stereoselective total synthesis of fully hydroxy-protected mycolactones A and B and their stereoisomerization upon deprotection［J］. Chem Eur J, 2011,17:4118-4130.
【5】FOW K L, POON L C H, SIM S T, et al. Enhanced asymmetric reduction of ethyl 3-oxobutyrate by baker′s yeast via substrate feeding and enzyme inhibition［J］. Engineering in Life Sciences, 2008,8(4):372-380.
【6】Eastman Chemical Company. Chiral ruthenium complexes of phosphine-aminophosphine ligands for asymmetric hydrogenation of 1,3-dicarbonyl compounds: USA, US6939981B1［P］. 2005-09-06.
【7】施介华,程向炜,周亮,等.柱前衍生化法分离3-羟基丁酸乙酯光学异构体［J］.分析化学, 2007,35(5):714-718.
【8】何成,许建和,刘幽燕,等.固定化酵母非水相催化羰基不对称还原反应的研究［J］.化学研究与应用, 2001,13(6):632-635.
【9】MILLOT N, BORMAN P, ANSON M S, et al. Rapid determination of enantiomeric excess using infrared thermography［J］. Org Process Res, 2002,6:463-470.
【10】SALUZZO C, LAMOUILLE T, HERAULT D, et al. Polymer-supported catalysts: enantioselective hydrogenation and hydrogen transfer reduction［J］. Bioorg Med Chem Lett, 2002,12:1841-1844.
【11】SAWAMURA M, KUWANO R, SHIRAI J, et al. Asymmetric hydrosilylation of keto esters catalyzed by a rhodium complex with trans-chelating chiral diphosphine EtTRAP［J］. Synlett, 1995:347-348.
【2】厦门大学.一种高对映体纯松叶蜂性信息素与立体异构体的合成方法:中国,CN102167666A［P］. 2011-08-31.
【3】HATANAKA M, NITTA H. Synthetic studies on thienamycin and 1β-methylcarbapenem starting from (R)-3-hydroxybutyrate［J］. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 1986,28:542-549.
【4】WANG Guang-wei, YING Nin, NEGISHI E. Highly stereoselective total synthesis of fully hydroxy-protected mycolactones A and B and their stereoisomerization upon deprotection［J］. Chem Eur J, 2011,17:4118-4130.
【5】FOW K L, POON L C H, SIM S T, et al. Enhanced asymmetric reduction of ethyl 3-oxobutyrate by baker′s yeast via substrate feeding and enzyme inhibition［J］. Engineering in Life Sciences, 2008,8(4):372-380.
【6】Eastman Chemical Company. Chiral ruthenium complexes of phosphine-aminophosphine ligands for asymmetric hydrogenation of 1,3-dicarbonyl compounds: USA, US6939981B1［P］. 2005-09-06.
【7】施介华,程向炜,周亮,等.柱前衍生化法分离3-羟基丁酸乙酯光学异构体［J］.分析化学, 2007,35(5):714-718.
【8】何成,许建和,刘幽燕,等.固定化酵母非水相催化羰基不对称还原反应的研究［J］.化学研究与应用, 2001,13(6):632-635.
【9】MILLOT N, BORMAN P, ANSON M S, et al. Rapid determination of enantiomeric excess using infrared thermography［J］. Org Process Res, 2002,6:463-470.
【10】SALUZZO C, LAMOUILLE T, HERAULT D, et al. Polymer-supported catalysts: enantioselective hydrogenation and hydrogen transfer reduction［J］. Bioorg Med Chem Lett, 2002,12:1841-1844.
【11】SAWAMURA M, KUWANO R, SHIRAI J, et al. Asymmetric hydrosilylation of keto esters catalyzed by a rhodium complex with trans-chelating chiral diphosphine EtTRAP［J］. Synlett, 1995:347-348.
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