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Absence of reverse anomeric effect in furanosides

Grundberg, Hans LU ; Eriksson-Bajtner, Johan ; Bergquist, Karl-Erik LU ; Sundin, Anders LU and Ellervik, Ulf LU (2006) In Journal of Organic Chemistry 71(16). p.5892-5896
Abstract
A series of conformationally restricted N-"furanosides" has been synthesized, where the carbons of the tetrahydrofuran ring are kept in one plane by a rigid norbornane skeleton, permitting only the ring oxygen to move above or below the tetrahydrofuran ring plane. This causes the substituents of the anomeric carbon to occupy a pseudoaxial or a pseudoequatorial position. On protonation of these "norbornane-furanosides" with trifluoromethanesulfonic acid, all three compounds exhibited decreasing coupling constants for the anomeric proton, indicating a shift toward the pseudoaxial conformation. The coupling constant measurements were supported by volume integration of NOESY cross-peaks, which also showed a change toward the pseudoaxial... (More)
A series of conformationally restricted N-"furanosides" has been synthesized, where the carbons of the tetrahydrofuran ring are kept in one plane by a rigid norbornane skeleton, permitting only the ring oxygen to move above or below the tetrahydrofuran ring plane. This causes the substituents of the anomeric carbon to occupy a pseudoaxial or a pseudoequatorial position. On protonation of these "norbornane-furanosides" with trifluoromethanesulfonic acid, all three compounds exhibited decreasing coupling constants for the anomeric proton, indicating a shift toward the pseudoaxial conformation. The coupling constant measurements were supported by volume integration of NOESY cross-peaks, which also showed a change toward the pseudoaxial conformation upon protonation of the nitrogen. These results provide no evidence for the so-called reverse anomeric effect; on the contrary they are in full agreement with a small normal anomeric effect. (Less)
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organization
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type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
71
issue
16
pages
5892 - 5896
publisher
The American Chemical Society (ACS)
external identifiers
  • wos:000239336600009
  • scopus:33746922772
  • pmid:16872169
ISSN
1520-6904
DOI
10.1021/jo060436i
language
English
LU publication?
yes
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The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
id
25a12eb6-5140-4f1d-b161-4936d015dda2 (old id 399481)
date added to LUP
2016-04-01 11:58:00
date last changed
2020-01-12 08:57:17
@article{25a12eb6-5140-4f1d-b161-4936d015dda2,
  abstract     = {A series of conformationally restricted N-"furanosides" has been synthesized, where the carbons of the tetrahydrofuran ring are kept in one plane by a rigid norbornane skeleton, permitting only the ring oxygen to move above or below the tetrahydrofuran ring plane. This causes the substituents of the anomeric carbon to occupy a pseudoaxial or a pseudoequatorial position. On protonation of these "norbornane-furanosides" with trifluoromethanesulfonic acid, all three compounds exhibited decreasing coupling constants for the anomeric proton, indicating a shift toward the pseudoaxial conformation. The coupling constant measurements were supported by volume integration of NOESY cross-peaks, which also showed a change toward the pseudoaxial conformation upon protonation of the nitrogen. These results provide no evidence for the so-called reverse anomeric effect; on the contrary they are in full agreement with a small normal anomeric effect.},
  author       = {Grundberg, Hans and Eriksson-Bajtner, Johan and Bergquist, Karl-Erik and Sundin, Anders and Ellervik, Ulf},
  issn         = {1520-6904},
  language     = {eng},
  number       = {16},
  pages        = {5892--5896},
  publisher    = {The American Chemical Society (ACS)},
  series       = {Journal of Organic Chemistry},
  title        = {Absence of reverse anomeric effect in furanosides},
  url          = {http://dx.doi.org/10.1021/jo060436i},
  doi          = {10.1021/jo060436i},
  volume       = {71},
  year         = {2006},
}