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Copper-Free Huisgen 1,3-Dipolar Cycloaddition to 3-Benzotriazolo-3-Deoxy-β-D-Galactopyranosides – Cyclization of a Secondary Azide and Benzyne

Öberg, Christopher LU ; Leffler, Hakon LU and Nilsson, Ulf LU (2010) In Trends in Carbohydrate Research 2(2). p.1-4
Abstract
Methyl 2-O-acetyl-3-benzotriazolo-4,6-O-benzylidene-3-deoxy- β -D-galactopyranoside was assembled by reacting benzyne, from 2-trimethylsilyl-trifluoromethansulfonylbenzene, and a secondary galactopyranoside azide in a copper-free Huisgen 1,3-dipolar cycloaddition. Following deprotection, the resulting benzotriazoles were evaluated as galectin inhibitors resulting in a 2-4 fold increase in affinity against galectin-1, -2 and -4 N-terminus compared to the parent methyl galactoside.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Trends in Carbohydrate Research
volume
2
issue
2
pages
1 - 4
publisher
Association of Carbohydrate Chemists and Technologists
ISSN
0975-0304
language
English
LU publication?
yes
id
19b7ab7a-ec2a-4b83-80c5-b9a6e53ceb8f (old id 1698123)
alternative location
http://www.trendscarbo.com/view_paper_all.php?id=829877055
date added to LUP
2010-10-22 12:51:23
date last changed
2016-04-16 07:11:11
@misc{19b7ab7a-ec2a-4b83-80c5-b9a6e53ceb8f,
  abstract     = {Methyl 2-O-acetyl-3-benzotriazolo-4,6-O-benzylidene-3-deoxy- β -D-galactopyranoside was assembled by reacting benzyne, from 2-trimethylsilyl-trifluoromethansulfonylbenzene, and a secondary galactopyranoside azide in a copper-free Huisgen 1,3-dipolar cycloaddition. Following deprotection, the resulting benzotriazoles were evaluated as galectin inhibitors resulting in a 2-4 fold increase in affinity against galectin-1, -2 and -4 N-terminus compared to the parent methyl galactoside.},
  author       = {Öberg, Christopher and Leffler, Hakon and Nilsson, Ulf},
  issn         = {0975-0304},
  language     = {eng},
  number       = {2},
  pages        = {1--4},
  publisher    = {ARRAY(0x9d53da0)},
  series       = {Trends in Carbohydrate Research},
  title        = {Copper-Free Huisgen 1,3-Dipolar Cycloaddition to 3-Benzotriazolo-3-Deoxy-β-D-Galactopyranosides – Cyclization of a Secondary Azide and Benzyne},
  volume       = {2},
  year         = {2010},
}