氨基糖的立体选择性合成路线:利用通用多功能手性支架的不同方法

Synthesis Pub Date : 2024-07-22 DOI:10.1055/a-2353-1618
Srinath Pashikanti, Apurba Datta
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引用次数: 0

摘要

从一种由 l-丝氨酸衍生的多功能氨基丁烯内酯作为常见的手性结构单元开始,我们开发出了具有代表性的二羟基、三羟基和四羟基亚氨基糖的立体选择性合成路线。合成路线的关键步骤包括分子内氨溶协议以形成杂杂环核心,以及在哌啶环的不同位置安装所需的取代基,使驻留的烯分子官能化。所描述的策略和方法有望为各种具有结构和药物化学意义的亚氨基糖支架提供灵活的合成途径。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Stereoselective Synthetic Routes to Iminosugars: A Divergent Approach Utilizing a Common Multifunctional Chiral Scaffold

Stereoselective Synthetic Routes to Iminosugars: A Divergent Approach Utilizing a Common Multifunctional Chiral Scaffold

Starting from an l-serine-derived multifunctional aminobutenolide as a common chiral building block, stereoselective synthetic routes to representative examples of di-, tri-, and tetrahydroxylated iminosugars have been developed. Key steps in the synthetic routes involved an intramolecular aminolysis protocol to form the azaheterocyclic core, and functionalization of a resident alkene moiety towards installation of the desired substituents at the various positions of the piperidine ring. The strategy and the approach described are expected to provide flexible synthetic routes to various iminosugar scaffolds of structural and medicinal chemical significance.

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