First total chemical synthesis of natural acyl derivatives of some phenolglycosides of the family Salicaceae

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14 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)66-72
Number of pages7
JournalCarbohydrate Research
Volume363
DOIs
Publication statusPublished - 1 Dec 2012

Keywords

  • Glycosylation
  • Phenolic glycosides
  • Populosides A, B, C
  • Protective group cleavage
  • Salireposide

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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