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Aryl Sulfonates in Inversions at Secondary Carbohydrate Hydroxyl Groups: A New and Improved Route Toward 3-Azido-3-deoxy-beta-D-galactopyranosides

Peterson, Kristoffer LU ; Weymouth-Wilson, Alex and Nilsson, Ulf LU (2015) In Journal of Carbohydrate Chemistry 34(8). p.490-499
Abstract
A method of using benzenesulfonates and imidazylates as leaving groups at the secondary C3 galactopyranose carbon, instead of the commonly used less stable triflate leaving group, to facilitate scale-up and improve reproducibility is disclosed. The benzenesulfonates and imidazylates were proven to be significantly more stable than the corresponding triflates and the method was used to devise an improved route toward 3-azido-3-deoxy-beta-D-galactopyranosides.
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
Benzenesulfonates, Imidazylates, Inversion, Galactose
in
Journal of Carbohydrate Chemistry
volume
34
issue
8
pages
490 - 499
publisher
Marcel Dekker
external identifiers
  • wos:000366302500004
  • scopus:84949725520
ISSN
0732-8303
DOI
10.1080/07328303.2015.1105248
language
English
LU publication?
yes
id
f44f6c48-d7be-41e0-af2c-c09f32a3dce4 (old id 8559964)
date added to LUP
2016-04-01 13:56:06
date last changed
2022-01-27 21:54:55
@article{f44f6c48-d7be-41e0-af2c-c09f32a3dce4,
  abstract     = {{A method of using benzenesulfonates and imidazylates as leaving groups at the secondary C3 galactopyranose carbon, instead of the commonly used less stable triflate leaving group, to facilitate scale-up and improve reproducibility is disclosed. The benzenesulfonates and imidazylates were proven to be significantly more stable than the corresponding triflates and the method was used to devise an improved route toward 3-azido-3-deoxy-beta-D-galactopyranosides.}},
  author       = {{Peterson, Kristoffer and Weymouth-Wilson, Alex and Nilsson, Ulf}},
  issn         = {{0732-8303}},
  keywords     = {{Benzenesulfonates; Imidazylates; Inversion; Galactose}},
  language     = {{eng}},
  number       = {{8}},
  pages        = {{490--499}},
  publisher    = {{Marcel Dekker}},
  series       = {{Journal of Carbohydrate Chemistry}},
  title        = {{Aryl Sulfonates in Inversions at Secondary Carbohydrate Hydroxyl Groups: A New and Improved Route Toward 3-Azido-3-deoxy-beta-D-galactopyranosides}},
  url          = {{https://lup.lub.lu.se/search/files/37164653/Peterson_accepted.pdf}},
  doi          = {{10.1080/07328303.2015.1105248}},
  volume       = {{34}},
  year         = {{2015}},
}