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:
https://lup.lub.lu.se/record/405699
- author
- Jacobsson, Mårten
LU
; Malmberg, Jesper
LU
and Ellervik, Ulf
LU
- organization
- publishing date
- 2006
- 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
- 2024-06-18 08:16:55
@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}},
keywords = {{halide; trichloroacetimidate; anomeric acetate; glycosylation; aromatic}},
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}},
}