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

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13 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

Fingerprint

Salicaceae
Benzyl Alcohol
Phenols
Biological Products
Acetates
Derivatives
Glucose
2,5-dihydroxybenzyl alcohol
salicyl alcohol

Keywords

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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

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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.",
keywords = "Glycosylation, Phenolic glycosides, Populosides A, B, C, Protective group cleavage, Salireposide",
author = "Belyanin, {Maxim L.} and Stepanova, {Elena Vledimirovna} and Ogorodnikov, {Vladimir D.}",
year = "2012",
month = "12",
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doi = "10.1016/j.carres.2012.10.006",
language = "English",
volume = "363",
pages = "66--72",
journal = "Carbohydrate Research",
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publisher = "Elsevier BV",

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TY - JOUR

T1 - First total chemical synthesis of natural acyl derivatives of some phenolglycosides of the family Salicaceae

AU - Belyanin, Maxim L.

AU - Stepanova, Elena Vledimirovna

AU - Ogorodnikov, Vladimir D.

PY - 2012/12/1

Y1 - 2012/12/1

N2 - 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.

AB - 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.

KW - Glycosylation

KW - Phenolic glycosides

KW - Populosides A, B, C

KW - Protective group cleavage

KW - Salireposide

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JO - Carbohydrate Research

JF - Carbohydrate Research

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