使用(2-硝基苯基)乙酰基保护的葡萄糖亚氨酯供体对不稳定天然产物进行化学糖基化反应

Weber Julia, Schwarz Markus, Schiefer Andrea, Hametner Christian, Häubl Georg, Fröhlich Johannes, Mikula Hannes

Institute of Applied Synthetic Chemistry Vienna University of Technology (TU Wien) Getreidemarkt 9 1060 Vienna Austria.

Romer Labs Technopark 1 3430 Tulln/Donau Austria.

European J Org Chem. 2018 Jun 7;2018(20-21):2701-2706. doi: 10.1002/ejoc.201800260. Epub 2018 Apr 26.

The synthesis of (2-nitrophenyl)acetyl (NPAc)-protected glucosyl donors is described that were designed for the neighboring-group assisted glucosylation of base-labile natural products also being sensitive to hydrogenolysis. Glycosylation conditions were optimized using a trichloroacetimidate glucosyl donor, and cyclohexylmethanol and (+)-menthol as model acceptors. The approach was then extended to a one-pot procedure for the synthesis of 1,2--glycosides. This method was finally applied for improved synthesis of the masked mycotoxin T2--β,d-glucoside.

描述了(2-硝基苯基)乙酰基(NPAc)保护的葡萄糖基供体的合成，这些供体是为对碱不稳定且对氢解敏感的天然产物的邻基辅助糖基化而设计的。使用三氯乙酰亚胺葡萄糖基供体、环己基甲醇和(+)-薄荷醇作为模型受体优化了糖基化条件。然后将该方法扩展到一锅法合成1,2-糖苷。该方法最终应用于改进掩蔽霉菌毒素T2-β,d-葡萄糖苷的合成。