The Synthesis of Aryl-β-C-Glycosides from Native Saccharides.

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.