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对称和不对称溶血双磷脂酸衍生物的合成。

Syntheses of Symmetrical and Unsymmetrical Lysobisphosphatidic Acid Derivatives.

作者信息

Chinthapally Kiran, Blagg Brian S J, Ashfeld Brandon L

机构信息

Warren Family Center for Drug Discovery and Development, University of Notre Dame, Notre Dame, Indiana 46556, United States.

Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States.

出版信息

J Org Chem. 2022 Aug 5;87(15):10523-10530. doi: 10.1021/acs.joc.2c01176. Epub 2022 Jul 27.

Abstract

Recent years have witnessed significant achievements in the field of organic chemistry, which have led to new drugs and the discovery of new and biologically interesting molecules. Herein, we describe a practical and efficient approach to the synthesis of enantiomerically pure and diverse lysobisphosphatidic acid analogues. The key feature of the synthesis is a one-pot, sequential phosphorylation of a protected -2--oleoyl glycerol or -3--oleoyl glycerol with 2-cyanoethyl ,-diisopropylchlorophosphoramidite, followed by oxidation.

摘要

近年来,有机化学领域取得了重大成就,这些成就带来了新药物以及新的、具有生物学意义的分子的发现。在此,我们描述了一种实用且高效的方法,用于合成对映体纯的多种溶血双磷脂酸类似物。该合成方法的关键特征是将受保护的 -2--油酰甘油或 -3--油酰甘油与 2-氰基乙基 ,-二异丙基氯代亚磷酰胺进行一锅法连续磷酸化,随后进行氧化。

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