| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1383948 | Carbohydrate Research | 2012 | 7 Pages |
The total synthesis of certain natural phenolglycosides of the family Salicaceae, namely: salireposide, populosides A, B, and C and not occurring in plants desoxysalireposide (2-(β-d-glucopyranosyloxy)-benzylbenzoate) and per-acetate of iso-salireposide (2-(β-d-glucopyranosyloxy)-5-benzoyloxy benzyl alcohol), starting from readily available phenols and glucose was accomplished. A simple method for the synthesis of phenolglycosides derivatives of 2-acyloxy salicyl and gentisyl alcohol was developed. The key step of these natural products’ synthesis is a selective removal of acetyl groups in the presence of other acyl groups.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Total synthesis of natural phenolglycosides from available substrates is reported. ► Synthetic phenolglycosides are proved to be identical to natural phenolglycosides. ► We report acid-catalyzed acetyl group cleavage without breaking the glycosidic bond.
