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Synthesis of 3-azido-3-deoxy-beta-d-galactopyranosides.

Öberg, Christopher LU ; Noresson, Ann-Louise LU ; Delaine, Tamara LU ; Larumbe, Amaia; Tejler, Johan LU ; von Wachenfeldt, Henrik LU and Nilsson, Ulf LU (2009) In Carbohydrate Research 344(11). p.1282-1284
Abstract
Three efficient routes to 3-azido-3-deoxy-beta-d-galactopyranosides were developed relying on a double inversion protocol at C3. Two of the routes were demonstrated to work with both O- and S-glycosides. In all three routes, the 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-beta-d-galactopyranosides were obtained by an azide inversion of the key intermediates 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-d-gulopyranosides. The intermediate gulopyranosides were in turn obtained from 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-d-galactopyranosides, installed in one pot from the 4,6-O-benzylidene-beta-d-galactopyranosides, by inversion with nitrite or acetate. For O-glycosides, the gulopyranoside... (More)
Three efficient routes to 3-azido-3-deoxy-beta-d-galactopyranosides were developed relying on a double inversion protocol at C3. Two of the routes were demonstrated to work with both O- and S-glycosides. In all three routes, the 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-beta-d-galactopyranosides were obtained by an azide inversion of the key intermediates 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-d-gulopyranosides. The intermediate gulopyranosides were in turn obtained from 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-d-galactopyranosides, installed in one pot from the 4,6-O-benzylidene-beta-d-galactopyranosides, by inversion with nitrite or acetate. For O-glycosides, the gulopyranoside configuration could alternatively be obtained from the 4,6-O-benzylidene-beta-d-galactopyranoside by elimination to give the 2,3-dianhydro derivative followed by a highly stereoselective cis-dihydroxylation. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Carbohydrate Research
volume
344
issue
11
pages
1282 - 1284
publisher
Elsevier
external identifiers
  • wos:000268431400003
  • pmid:19505681
  • scopus:67649443901
ISSN
1873-426X
DOI
10.1016/j.carres.2009.05.005
language
English
LU publication?
yes
id
3a24f324-eb94-4743-b5f9-eb7a601c9535 (old id 1434411)
date added to LUP
2009-07-08 12:07:02
date last changed
2017-02-05 03:41:15
@article{3a24f324-eb94-4743-b5f9-eb7a601c9535,
  abstract     = {Three efficient routes to 3-azido-3-deoxy-beta-d-galactopyranosides were developed relying on a double inversion protocol at C3. Two of the routes were demonstrated to work with both O- and S-glycosides. In all three routes, the 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-beta-d-galactopyranosides were obtained by an azide inversion of the key intermediates 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-d-gulopyranosides. The intermediate gulopyranosides were in turn obtained from 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-d-galactopyranosides, installed in one pot from the 4,6-O-benzylidene-beta-d-galactopyranosides, by inversion with nitrite or acetate. For O-glycosides, the gulopyranoside configuration could alternatively be obtained from the 4,6-O-benzylidene-beta-d-galactopyranoside by elimination to give the 2,3-dianhydro derivative followed by a highly stereoselective cis-dihydroxylation.},
  author       = {Öberg, Christopher and Noresson, Ann-Louise and Delaine, Tamara and Larumbe, Amaia and Tejler, Johan and von Wachenfeldt, Henrik and Nilsson, Ulf},
  issn         = {1873-426X},
  language     = {eng},
  number       = {11},
  pages        = {1282--1284},
  publisher    = {Elsevier},
  series       = {Carbohydrate Research},
  title        = {Synthesis of 3-azido-3-deoxy-beta-d-galactopyranosides.},
  url          = {http://dx.doi.org/10.1016/j.carres.2009.05.005},
  volume       = {344},
  year         = {2009},
}