Synthese de la cyclo-5'-8 desoxy-5' adenosine: stereochimie et mecanisme de la cyclisation d'un derive de l'iodo-5' adenosine par le zinc |
| |
Authors: | J Zylber R Pontikis A Merrien C Merienne M Baran-Marszak A Gaudemer |
| |
Institution: | Université Paris-Sud, Centre d''Orsay, L.A. 255, 91405 Orsay, France, Groupe de Recherche No. 12, CNRS, rue Henry-Dunant, 94320 Thiais, France |
| |
Abstract: | N,N'-Dibenzoyl 2', 3'-O-isopropylidene 5'-deoxy 5'-iodo adenosine can efficiently transformed into the corresponding 5',8-cyclo-7,8-dihydronucleoside by zinc in pyridine. Only one diastereoisomer is obtained. By spin decoupling and NOE techniques at 250 MHz, the R-configuration at C-8 was established. This compound showed typical dihedral angles of about 90° for the vicinal protons H-1', H-2' and H-3', H-4'. Using adenosine derivatives stereospecifically labelled at C-5', it was demonstrated that the cyclisation occurs with racemisation at that position. |
| |
Keywords: | Adresse actuelle: ICSN CNRS 91190 Gif-sur-Yvette France |
本文献已被 ScienceDirect 等数据库收录! |
|