• Spin labelled C-glycoside analogs : derivatives of 1,4-anhydro-4-deoxy-2,3-O-cyclopentylidene-1,4-N-hydroxyimino-DL-erythrofuranose
    J.M.J. Tronchet, M. Balkadjian, G. Zosimo-Landolfo, F. Barbalat-Rey, P. Lichtle, A. Ricca, I. Komaromi, G. Bernardinelli and M. Geoffroy
    Journal of Carbohydrate Chemistry, 14 (1) (1995), p17-34
    DOI:10.1080/07328309508006434 | unige:2844 | Abstract | Article PDF
A series of 2,3-O-cyclopentylidene C-glycoside analogs in which the furanose ring has been replaced with a N-hydroxypyrrolidine have been prepared. A structural study of these tricyclic compounds and the aminoxyl radicals thereof has been carried out using variable temperature 1H NMR, X-ray diffraction, molecular dynamics and EPR spectroscopy. Both types of compounds, N-hydroxypyrrolidines and pyrrolidine N-oxyls, fundamentally prefer - in solutions- N-endo conformations over the alternate, N-exo forms found by X-ray diffraction studies and computed to be more stable by molecular dynamics.

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