Aldol Reactions of Biorenewable Triacetic Acid Lactone Precursor Evaluated Using Desorption Electrospray Ionization Mass Spectrometry High-Throughput Experimentation and Validated by Continuous Flow Synthesis

H. Samuel  Ewan; Shruti A.  Biyani; Jaycie  DiDomenico; David  Logsdon; Tiago J. P.  Sobreira; Larisa  Avramova; R. Graham  Cooks; David H.  Thompson

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Aldol Reactions of Biorenewable Triacetic Acid Lactone Precursor Evaluated Using Desorption Electrospray Ionization Mass Spectrometry High-Throughput Experimentation and Validated by Continuous Flow Synthesis

机译：使用解吸电喷雾电离质谱高通量实验评估生物治疗三转醋酸内酯前体的醛醇反应，并通过连续流动合成验证

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Desorption electrospray ionization-mass spectrometry (DESI-MS) was used as a high-throughput experimentation (HTE) tool to rapidly identify derivatives of the biobased platform molecule triacetic acid lactone (TAL). TAL is a platform molecule capable of conversion to a wide range of useful commodity chemicals, agrochemicals, and advanced pharmaceutical intermediates. In the present study, a diverse family of aldol reaction mixtures were prepared in high-density microtiter plates with a liquid handling robot, then printed with a pin tool onto a PTFE surface for analysis by DESI-MS. Our DESI-MS results indicate that aldol products of TAL were obtained for each substrate tested, in good agreement with previously reported TAL reactivity. These HTE experiments also revealed solvent-dependent reactivity trends that facilitated reaction scale up. Our findings suggest that DESI-MS analysis can rapidly inform the selection of optimal reaction conditions from a wide variety of conditions for scale up using continuous synthesis conditions.

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《ACS combinatorial science》 |2020年第12期|共8页
作者
H. Samuel Ewan; Shruti A. Biyani; Jaycie DiDomenico; David Logsdon; Tiago J. P. Sobreira; Larisa Avramova; R. Graham Cooks; David H. Thompson;
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作者单位

Department of Chemistry Purdue University Purdue University Center for Cancer Research Multidisciplinary Cancer Research Facility Bindley Bioscience Center;

Department of Chemistry Purdue University Purdue University Center for Cancer Research Multidisciplinary Cancer Research Facility Bindley Bioscience Center;

Department of Chemistry Purdue University Purdue University Center for Cancer Research Multidisciplinary Cancer Research Facility Bindley Bioscience Center;

Department of Chemistry Purdue University Purdue University Center for Cancer Research Multidisciplinary Cancer Research Facility Bindley Bioscience Center;

Department of Chemistry Purdue University Purdue University Center for Cancer Research Multidisciplinary Cancer Research Facility Bindley Bioscience Center;

Department of Chemistry Purdue University Purdue University Center for Cancer Research Multidisciplinary Cancer Research Facility Bindley Bioscience Center;

Department of Chemistry Purdue University Purdue University Center for Cancer Research Multidisciplinary Cancer Research Facility Bindley Bioscience Center;

Department of Chemistry Purdue University Purdue University Center for Cancer Research Multidisciplinary Cancer Research Facility Bindley Bioscience Center;

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原文格式 PDF
正文语种 eng
中图分类化学;
关键词
triacetic acid lactone; platform chemical; high-throughput experiment; desorption electrospray ionization; MS/MS; aldol reaction;

机译：三乙酸内酯;平台化学;高通量实验;解吸电喷雾电离;MS / MS;aldol反应;

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Aldol Reactions of Biorenewable Triacetic Acid Lactone Precursor Evaluated Using Desorption Electrospray Ionization Mass Spectrometry High-Throughput Experimentation and Validated by Continuous Flow Synthesis

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