Unprecedented formation of 8(R),5′-O-cycloribonucleosides through a triflation reaction of purine ribonucleosides

Claire Amiable (1, 2) , Sylvie Pochet (1)

1 Chimie et Biocatalyse
2 UPD5 - Université Paris Descartes - Paris 5

The present paper describes the formation of N-triflyl-7,8-dihydro-8(R),5′-O-cyclonucleosides during our efforts to introduce the triflate leaving group at the 5′-position of purine ribonucleoside derivatives. The chemical structure of these original cyclonucleosides, including the absolute configuration at C-8, was unambiguously elucidated by elemental analysis, high-resolution mass spectrometry, NMR analysis and X-ray crystallography. Our results bring new insights into the reactivity of the 5′-O-triflate derivatives of purine ribonucleosides while providing an efficient access to original cyclonucleosides.

Domaines: Chimie organique

Claire Amiable, Sylvie Pochet. Unprecedented formation of 8(R),5′-O-cycloribonucleosides through a triflation reaction of purine ribonucleosides. Tetrahedron, 2015, 71 (17), pp.2525-2529. ⟨10.1016/j.tet.2015.03.020⟩. ⟨hal-01968373⟩