Synthesis of Methyl Aprabiosaminide and 2-Hydroxyapramycin from Apramycin.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-02-14 DOI:10.1021/acs.orglett.5c00168

Niteshlal Kasdekar, Michael R Spieker, Andrea Vasella, Sven N Hobbie, David Crich

引用次数: 0

Abstract

We describe a protocol for the selective cleavage of the 2-deoxystreptamine ring from the structurally unusual aminoglycoside antibiotic apramycin, enabling for the first time the preparation of aprabiosamine derivatives. We further describe reglycosylation of the aprabiosamine core with a selectively protected optically pure streptamine derivative, giving, after deprotection, 2-hydroxyapramycin, the first apramycin derivative functionalized at the 2 position.

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我们介绍了一种选择性裂解结构特殊的氨基糖苷类抗生素阿普霉素中 2-脱氧链霉胺环的方法，从而首次制备出了阿普霉素衍生物。我们进一步描述了用一种选择性保护的光学纯链霉胺衍生物对阿普拉比奥沙明核心进行再糖基化，在去保护后得到 2-羟基阿普拉霉素，这是第一种在 2 位功能化的阿普拉霉素衍生物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.