Cloutier, Maude; Lavoie, Serge et Gauthier, Charles 
ORCID: https://orcid.org/0000-0002-2475-2050
(2022).
C7 Epimerization of Benzylidene-Protected β-d-Idopyranosides Brings Structural Insights into Idose Conformational Flexibility
Journal of Organic Chemistry
, vol. 87
, nº 19.
pp. 12932-12953.
DOI: 10.1021/acs.joc.2c01504.
Résumé
Idose is unique among other aldohexoses because of its high conformational flexibility in solution. We herein show that benzylidene acetal-protected 3-O-acyl-β-d-idopyranosides undergo Lewis acid-catalyzed C7 epimerization with concomitant (4)C(1) to (1)C(4) ring inversion. The reaction conditions and structural parameters for this transformation to occur have been thoroughly investigated through an extensive glycosylation study combined with NMR analyses, X-ray diffraction, and quantum molecular modeling. In addition to reporting a direct, β-stereoselective idosylation approach, our work brings fundamental structural insights into the conformational flexibility of idose.
| Type de document: | Article |
|---|---|
| Mots-clés libres: | - |
| Centre: | Centre INRS-Institut Armand Frappier |
| Date de dépôt: | 08 déc. 2023 21:58 |
| Dernière modification: | 08 déc. 2023 21:58 |
| URI: | https://espace.inrs.ca/id/eprint/13360 |
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