Bunt Daan V, van Looij Joey, Lenze Alexander F, Štuhec Viktor, Witte Martin D, Minnaard Adriaan J
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands.
Chemistry. 2025 Jul 2;31(37):e202501216. doi: 10.1002/chem.202501216. Epub 2025 May 30.
The synthesis of p-nitrophenol-β-C-glycosides from native mono-, di-, and trisaccharides is described. The one-pot-two-step procedure uses water as the solvent and produces exclusively β-C-glycosides, the desired stereochemistry for most medicinal chemistry applications. The versatility of the approach is illustrated by the synthesis of the nanomolar SGLT2 inhibitor [3-(4-ethylbenzyl)phenyl]-β-C-glucoside.
描述了从天然单糖、二糖和三糖合成对硝基苯酚-β-C-糖苷的方法。一锅两步法以水为溶剂，专一性地生成β-C-糖苷，这是大多数药物化学应用所需的立体化学结构。通过合成纳摩尔级的SGLT2抑制剂[3-(4-乙基苄基)苯基]-β-C-葡萄糖苷，展示了该方法的通用性。
