title: First total chemical synthesis of natural acyl derivatives of some phenolglycosides of the family Salicaceae.
abstract: 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.
authors.affiliation: National Research Tomsk Polytechnic University, 30 Lenin Avenue, Tomsk 634050, Russia.
authors.forename: Maxim L
authors.initials: ML
authors.lastname: Belyanin
authors.forename: Elena V
authors.initials: EV
authors.lastname: Stepanova
authors.forename: Vladimir D
authors.initials: VD
authors.lastname: Ogorodnikov
mesh_terms: D001592:Benzyl Alcohols / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D005960:Glucosides / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006873:Hydroquinones / Q000737:chemistry; D031308:Salicaceae / Q000737:chemistry*
chemical_list: D001592:Benzyl Alcohols; D001688:Biological Products; D005960:Glucosides; D006027:Glycosides; D006873:Hydroquinones; C525285:salirepin; C005696:salicin