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Title

Synthesis and conformational analysis of a novel type of spin labelled bicyclonucleoside based on a tetrahydrofurano(2,3-c)pyrrolidine sugar skeleton
Authors
Tronchet, Jean Marcel Julien
Brenas-Chinchon, Laetitia
Barbalat, Françoise
Zsely Schaffter, Martina Maria
Geoffroy, Michel
Published in Nucleosides & Nucleotides. 1998, vol. 17, no. 6, p. 1019-1031
Abstract 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.
Keywords Drug design & development — Medicinal & pharmaceutical chemistry — Organic chemistry — Pharmaceutical science
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Structures
Faculté des sciences / Section des sciences pharmaceutiques
Faculté des sciences / Section de chimie et biochimie / Département de chimie physique
Research group Groupe Geoffroy
Citation
(ISO format) 		TRONCHET, Jean Marcel Julien et al. Synthesis and conformational analysis of a novel type of spin labelled bicyclonucleoside based on a tetrahydrofurano(2,3-c)pyrrolidine sugar skeleton. In: Nucleosides & Nucleotides, 1998, vol. 17, n° 6, p. 1019-1031. doi: 10.1080/07328319808004218 https://archive-ouverte.unige.ch/unige:2765

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Deposited on : 2009-09-21

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