• Synthesis and conformational analysis of a novel type of spin labelled bicyclonucleoside based on a tetrahydrofurano(2,3-c)pyrrolidine sugar skeleton
    J.M.J. Tronchet, L. Brenas, F. Barbalat-Rey, M. Zsély and M. Geoffroy
    Nucleosides, Nucleotides and Nucleic Acids, 17 (6) (1998), p1019-1031
    DOI:10.1080/07328319808004218 | unige:2765 | Abstract | Article PDF
Bicyclonucleosides bearing a 5-deoxy-5-N-hydroxyamino-3,N5-(1,1-ethano)-β-o-furanosyl sugar moiety (15-18) have been prepared by glycosidation of the corresponding bicyclosugars obtained via an intramolecular reverse Cope elimination. The configuration of the asymmetric carbon of the 1,1-ethano bridge is the most important factor directing the conformation of the N-hydroxypyrrolidine ring and its invertomers ratio as shown by variable temperature H NMR experiments.

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