Department of Chemistry, University of Redlands, 1200 E. Colton Avenue, Redlands, CA, 92374, USA.
Department of Chemistry, University of Redlands, 1200 E. Colton Avenue, Redlands, CA, 92374, USA.
Carbohydr Res. 2023 Oct;532:108904. doi: 10.1016/j.carres.2023.108904. Epub 2023 Jul 26.
The selective functionalization of carbohydrates provides a powerful method for introducing structural complexity, allowing access to unique drug scaffolds with distinctive pharmaceutical profiles. Herein, we describe an efficient and selective carbon-carbon bond forming reaction of a variety of common trimethylsilyl-protected pyranosides and pyranoses at C-6 using a one-pot Dess-Martin periodinane-mediated oxidation deprotection. This is followed by addition of stabilized and non-stabilized ylides to generate alkenoate carbohydrates and related analogs in good to moderate yields. We also report on the rapid deprotection of the remaining trimethylsilyl ether groups in near quantitative yields using an acidic resin-mediated ethanolysis.
碳水化合物的选择性功能化提供了一种强大的方法来引入结构复杂性，使独特的药物支架具有独特的药物特性。在此，我们描述了一种使用一锅法 Dess-Martin 过碘烷介导的氧化脱保护，在 C-6 位对各种常见的三甲基硅基保护的吡喃糖和吡喃糖进行高效和选择性碳-碳键形成反应的方法。接着，加入稳定和非稳定的叶立德，以良好至中等收率生成烯酸酯碳水化合物和相关类似物。我们还报告了使用酸性树脂介导的乙醇解，以近乎定量的收率快速脱除剩余的三甲基硅基醚基团。
