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Anomeric effects in pyranosides and related acetals

Gerber-Lemaire, Sandrine  
•
Vogel, Pierre  
Pilar Rauter, Amelia
•
Lindhorst, Thisbe
2009
Carbohydrate Chemistry. Chemical and Biological Approaches

The anomeric effect, originally defined as the preference of an electronegative substituent at the anomeric position of pyranosides to stand in an axial rather than an equatorial position, results from the combination of multiple steric, stereoelectronic and medium interactions. A more generalized definition of the enthalpic anomeric effect refers to the gem-dioxy stabilizing effect which makes acetals more stable than their 1,n-dialkoxyalkane isomers (n>1). This effect is far more important than the difference in stability between conformers of acetals as those found in axial and equatorial pyranoses and pyranosides. This review gives an up-dated view of enthalpic, conformational and also kinetic anomeric effects in pyranosides. The latter manifest themselves during heterolytical processes occuring at the anomeric centers of pyranosides and analogous compounds.

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Type
book part or chapter
DOI
10.1039/B905496K
Author(s)
Gerber-Lemaire, Sandrine  
Vogel, Pierre  
Editors
Pilar Rauter, Amelia
•
Lindhorst, Thisbe
Date Issued

2009

Publisher

RCS Publishing

Published in
Carbohydrate Chemistry. Chemical and Biological Approaches
Start page

13

End page

32

Volume
35
Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
September 8, 2009
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/42514
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