四纤维丝菌素C21 - C40片段四种立体异构体的氟代混合物合成
Fluorous Mixture Synthesis of Four Stereoisomers of the C21-C40 Fragment of Tetrafibricin.
作者信息
Zhang Kai, Curran Dennis P
机构信息
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA Fax +1(412)6249861.
出版信息
Synlett. 2010 Mar 1;2010(4):667-674. doi: 10.1055/s-0029-1219376.
Abstract
Four stereoisomers of the C21-C40 fragment are synthesized in a single exercise with the aid of fluorous tagging to encode configurations at C37 and C33. After demixing and detagging, the isomers were found to have substantially identical (1)H NMR spectra. However, there were some small but reliable differences in their (13)C NMR spectra.
摘要
借助氟代标记以编码C37和C33处的构型，在一次操作中合成了C21 - C40片段的四种立体异构体。在分离和去除标记后，发现这些异构体具有基本相同的¹H NMR谱。然而，它们的¹³C NMR谱存在一些微小但可靠的差异。
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2
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J Am Chem Soc. 2009 Apr 22;131(15):5411-3. doi: 10.1021/ja900849f.
3
Combinatorial synthesis of the 1,5-polyol system based on cross metathesis: structure revision of amphidinol 3.
Org Lett. 2008 Nov 20;10(22):5203-6. doi: 10.1021/ol802168r. Epub 2008 Oct 30.
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Angew Chem Int Ed Engl. 2008;47(6):1130-3. doi: 10.1002/anie.200704893.
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J Med Chem. 2007 Jun 28;50(13):2951-66. doi: 10.1021/jm061385k. Epub 2007 Jun 2.
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Chemistry. 2005 Aug 19;11(17):4866-80. doi: 10.1002/chem.200500076.
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