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Anomeric Effect in Furanosides. Experimental Evidence from Conformationally Restricted Compounds

Ellervik, Ulf LU orcid and Magnusson, Göran LU (1994) In Journal of the American Chemical Society 116. p.2340-2347
Abstract
A series of conformationally restricted 0-, C-, S-, and N-“furanosides” have been synthesized, where the number 3 and 4 carbons are part of a norbornane ring system. All the carbons of the tetrahydrofuran ring are kept in one plane by the rigid norbornane skeleton, permitting only the ring oxygen to move above or below the tetrahydrofuran ring plane. This causes the substituents on carbon 2 to occupy a pseudoaxial or a pseudoequatorial position. The “norbornane-furanosides” were investigated by NMR, X-ray crystallography, and molecular mechanics calculations. The O-and S-furanosides preferred the conformation with a pseudoaxial anomeric substituent, whereas its C-furanosidic counterpart preferred the conformation with a pseudoequatorial... (More)
A series of conformationally restricted 0-, C-, S-, and N-“furanosides” have been synthesized, where the number 3 and 4 carbons are part of a norbornane ring system. All the carbons of the tetrahydrofuran ring are kept in one plane by the rigid norbornane skeleton, permitting only the ring oxygen to move above or below the tetrahydrofuran ring plane. This causes the substituents on carbon 2 to occupy a pseudoaxial or a pseudoequatorial position. The “norbornane-furanosides” were investigated by NMR, X-ray crystallography, and molecular mechanics calculations. The O-and S-furanosides preferred the conformation with a pseudoaxial anomeric substituent, whereas its C-furanosidic counterpart preferred the conformation with a pseudoequatorial substituent. These findings constitute the first demonstration of a “by definition” anomeric effect in furanosides. © 1994, American Chemical Society. All rights reserved. (Less)
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type
Contribution to journal
publication status
published
subject
in
Journal of the American Chemical Society
volume
116
pages
2340 - 2347
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:0028197333
ISSN
1520-5126
DOI
10.1021/ja00085a013
language
English
LU publication?
yes
id
9bd9c79c-ece9-4666-87c5-2c5f3daa286e
date added to LUP
2023-08-10 15:05:26
date last changed
2024-01-05 04:06:27
@article{9bd9c79c-ece9-4666-87c5-2c5f3daa286e,
  abstract     = {{A series of conformationally restricted 0-, C-, S-, and N-“furanosides” have been synthesized, where the number 3 and 4 carbons are part of a norbornane ring system. All the carbons of the tetrahydrofuran ring are kept in one plane by the rigid norbornane skeleton, permitting only the ring oxygen to move above or below the tetrahydrofuran ring plane. This causes the substituents on carbon 2 to occupy a pseudoaxial or a pseudoequatorial position. The “norbornane-furanosides” were investigated by NMR, X-ray crystallography, and molecular mechanics calculations. The O-and S-furanosides preferred the conformation with a pseudoaxial anomeric substituent, whereas its C-furanosidic counterpart preferred the conformation with a pseudoequatorial substituent. These findings constitute the first demonstration of a “by definition” anomeric effect in furanosides. © 1994, American Chemical Society. All rights reserved.}},
  author       = {{Ellervik, Ulf and Magnusson, Göran}},
  issn         = {{1520-5126}},
  language     = {{eng}},
  pages        = {{2340--2347}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of the American Chemical Society}},
  title        = {{Anomeric Effect in Furanosides. Experimental Evidence from Conformationally Restricted Compounds}},
  url          = {{http://dx.doi.org/10.1021/ja00085a013}},
  doi          = {{10.1021/ja00085a013}},
  volume       = {{116}},
  year         = {{1994}},
}