Skip to main content

Lund University Publications

LUND UNIVERSITY LIBRARIES

Aromatic O-glycosylation

Jacobsson, Mårten LU ; Malmberg, Jesper LU and Ellervik, Ulf LU (2006) In Carbohydrate Research 341(10). p.1266-1281
Abstract
Carbohydrates carrying an aromatic aglycon are important natural products and thus key synthetic targets. However, due to the electron-withdrawing properties of aromatic rings, phenols are difficult to glycosylate. This review covers the most common carbohydrate donors used for aromatic O-glycosylation (anomeric acetates, halides, trichloroacetimidates and thioglycosides) as well as some less common donors. The scope of the review is to give practical examples of aromatic O-glycosylations and to offer guidelines for glycosylation of typical aromatic residues. Anomeric acetates or trichloroacetimidates, activated under acidic conditions, are preferred for electron rich aromatic aglycons, while glycosyl halides, activated using basic... (More)
Carbohydrates carrying an aromatic aglycon are important natural products and thus key synthetic targets. However, due to the electron-withdrawing properties of aromatic rings, phenols are difficult to glycosylate. This review covers the most common carbohydrate donors used for aromatic O-glycosylation (anomeric acetates, halides, trichloroacetimidates and thioglycosides) as well as some less common donors. The scope of the review is to give practical examples of aromatic O-glycosylations and to offer guidelines for glycosylation of typical aromatic residues. Anomeric acetates or trichloroacetimidates, activated under acidic conditions, are preferred for electron rich aromatic aglycons, while glycosyl halides, activated using basic conditions, are preferred for electron deficient aromatic residues. (c) 2006 Elsevier Ltd. All rights reserved. (Less)
Please use this url to cite or link to this publication:
author
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
halide, trichloroacetimidate, anomeric acetate, glycosylation, aromatic
in
Carbohydrate Research
volume
341
issue
10
pages
1266 - 1281
publisher
Elsevier
external identifiers
  • wos:000238563300005
  • pmid:16650391
  • scopus:33646925969
ISSN
1873-426X
DOI
10.1016/j.carres.2006.04.004
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
id
e0ee311f-4d84-470b-b365-853b8ee7f8fa (old id 405699)
date added to LUP
2016-04-01 12:05:25
date last changed
2021-09-22 03:16:43
@article{e0ee311f-4d84-470b-b365-853b8ee7f8fa,
  abstract     = {Carbohydrates carrying an aromatic aglycon are important natural products and thus key synthetic targets. However, due to the electron-withdrawing properties of aromatic rings, phenols are difficult to glycosylate. This review covers the most common carbohydrate donors used for aromatic O-glycosylation (anomeric acetates, halides, trichloroacetimidates and thioglycosides) as well as some less common donors. The scope of the review is to give practical examples of aromatic O-glycosylations and to offer guidelines for glycosylation of typical aromatic residues. Anomeric acetates or trichloroacetimidates, activated under acidic conditions, are preferred for electron rich aromatic aglycons, while glycosyl halides, activated using basic conditions, are preferred for electron deficient aromatic residues. (c) 2006 Elsevier Ltd. All rights reserved.},
  author       = {Jacobsson, Mårten and Malmberg, Jesper and Ellervik, Ulf},
  issn         = {1873-426X},
  language     = {eng},
  number       = {10},
  pages        = {1266--1281},
  publisher    = {Elsevier},
  series       = {Carbohydrate Research},
  title        = {Aromatic O-glycosylation},
  url          = {http://dx.doi.org/10.1016/j.carres.2006.04.004},
  doi          = {10.1016/j.carres.2006.04.004},
  volume       = {341},
  year         = {2006},
}