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五氟二醇的优化合成及通过三氟乙酸酯释放和卤化转化为α-吡喃葡萄糖。

Optimized Synthesis of a Pentafluoro--diol and Conversion to a -Glucopyranose through Trifluoroacetate-Release and Halogenation.

作者信息

Hazlitt Robert A, John Jinu P, Tran Que-Lynn, Colby David A

机构信息

Department of Chemistry, Purdue University, West Lafayette, Indiana, 47907, USA; Department of BioMolecular Sciences, University of Mississippi, Mississippi, 38677, USA.

Department of Chemistry, Purdue University, West Lafayette, Indiana, 47907, USA.

出版信息

Tetrahedron Lett. 2016 Apr 27;57(17):1906-1908. doi: 10.1016/j.tetlet.2016.03.064. Epub 2016 Mar 19.

DOI:10.1016/j.tetlet.2016.03.064
PMID:27182091
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4863236/
Abstract

Pentafluoro--diols are substrates that enable the synthesis of valuable difluoromethylene-containing organic molecules through the release of trifluoroacetate. Currently, only one synthetic strategy is available to assemble these important precursors. Herein, two new synthetic strategies to a complex pentafluoro--diol are compared to the existing route, and an improved synthetic route has completed. Moreover, the first synthesis of a -glucopyranose was finished by a tandem trifluoroacetate-release halogenation/cyclization protocol.

摘要

五氟二醇是一类底物,可通过释放三氟乙酸酯来合成有价值的含二氟亚甲基有机分子。目前,组装这些重要前体只有一种合成策略。在此,将两种合成复杂五氟二醇的新策略与现有路线进行了比较,并完成了一条改进的合成路线。此外,通过串联三氟乙酸酯释放卤化/环化方案首次完成了α-吡喃葡萄糖的合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7d1/4863236/63434685e5cb/nihms773144f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7d1/4863236/8ec89538e4eb/nihms773144f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7d1/4863236/6a487c655181/nihms773144f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7d1/4863236/57ffd4532133/nihms773144f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7d1/4863236/7d6397dbcf8c/nihms773144f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7d1/4863236/63434685e5cb/nihms773144f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7d1/4863236/8ec89538e4eb/nihms773144f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7d1/4863236/6a487c655181/nihms773144f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7d1/4863236/57ffd4532133/nihms773144f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7d1/4863236/7d6397dbcf8c/nihms773144f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7d1/4863236/63434685e5cb/nihms773144f5.jpg

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Angew Chem Int Ed Engl. 2015 Jan 26;54(5):1646-50. doi: 10.1002/anie.201410471. Epub 2014 Dec 4.
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9
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