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.

Original language	English
Pages (from-to)	66-72
Number of pages	7
Journal	Carbohydrate Research
Volume	363
DOIs	https://doi.org/10.1016/j.carres.2012.10.006
Publication status	Published - 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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10.1016/j.carres.2012.10.006

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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 = dec,

day = "1",

doi = "10.1016/j.carres.2012.10.006",

language = "English",

volume = "363",

pages = "66--72",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier BV",

}

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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