Synthesis and Conformational Analysis of A Novel Type of Spin Labelled Bicyclonucleoside Based on A Tetrahydrofurano[2,3-c]Pyrrolidine Sugar Skeleton

Jean M. J. Tronchet Departments of Organic Pharmaceutical Chemistry, University of Geneva, Sciences II, CH-1211, Geneva 4, Switzerland

Laetitia Brenas Departments of Organic Pharmaceutical Chemistry, University of Geneva, Sciences II, CH-1211, Geneva 4, Switzerland

Françoise Barbalat-Rey Departments of Organic Pharmaceutical Chemistry, University of Geneva, Sciences II, CH-1211, Geneva 4, Switzerland

Martina Zsély Departments of Organic Pharmaceutical Chemistry, University of Geneva, Sciences II, CH-1211, Geneva 4, Switzerland

Michel Geoffrey Departments of Physical Chemistry, University of Geneva, Sciences II, CH-1211, Geneva 4, Switzerland

Abstract

Bicyclonucleosides bearing a 5-deoxy-5-N-hydroxyamino-3,N ⁵-(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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Synthesis and Conformational Analysis of A Novel Type of Spin Labelled Bicyclonucleoside Based on A Tetrahydrofurano[2,3-c]Pyrrolidine Sugar Skeleton

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Synthesis and Conformational Analysis of A Novel Type of Spin Labelled Bicyclonucleoside Based on A Tetrahydrofurano[2,3-c]Pyrrolidine Sugar Skeleton

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