197298-02-5Relevant academic research and scientific papers
Diastereofacial Selective Addition of Ethynylcerium Reagent and Barton-McCombie Reaction as the Key Steps for the Synthesis of C-3′-Ethynylribonucleosides and of C-3′-Ethynyl-2′-deoxyribonucleosides
Jung, Pierre M. J.,Burger, Alain,Biellmann, Jean-Fran?ois
, p. 8309 - 8314 (2007/10/03)
We describe the preparation of 3′-alkynyluridine 4a and -adenosine 4b and of 3′-alkynyl-2′-deoxyuridine 16a and -adenosine 16b starting from the corresponding nucleosides. The desired stereochemistry of the C-3′ tertiary alcohol was obtained by reaction of an ethynylcerium-lithium reagent on a 3′-ketonucleoside with the hydroxyl group at C-5′ unprotected. The 2′-deoxygenation was performed by a Barton-McCombie reaction under appropriate conditions where the addition of tin hydride to the triple bond was suppressed. Evaluation of the anti-HIV activity of the C-3′ modified nucleosides is reported.
