Studies on Ribonucleoside Hydrogenphosphonates. Effect of a Vicinal Hydroxyl Function on the Stability of H-Phosphonate Diester Bond

Sophie Huss Laboratoire do Chimie Bio-Organique, U.A. No 488 du C.N.R.S., Université des Sciences of Techniques du Languedoc, Place Eugéne-Bataillon, 34060, Montpellier-Cédex, France

Gilles Gosselin Laboratoire do Chimie Bio-Organique, U.A. No 488 du C.N.R.S., Université des Sciences of Techniques du Languedoc, Place Eugéne-Bataillon, 34060, Montpellier-Cédex, France

Jacek Stawinski Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, 10691, Stockholm, Sweden

Roger Stromberg Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, 10691, Stockholm, Sweden

Jean-Louis Imbach Laboratoire do Chimie Bio-Organique, U.A. No 488 du C.N.R.S., Université des Sciences of Techniques du Languedoc, Place Eugéne-Bataillon, 34060, Montpellier-Cédex, France

Abstract

Stability of hydrogenphosphonate diester bond in the presence of a free vicinal hydroxyl function has been investigated on the example of ribonucleoside H-phosphonates. It was found that H-phosphonate diesters undergo immediate intramolecular cyclization, both with or without a base, affording 2′, 3′-cyclic H-phosphonate diesters.

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Studies on Ribonucleoside Hydrogenphosphonates. Effect of a Vicinal Hydroxyl Function on the Stability of H-Phosphonate Diester Bond

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Studies on Ribonucleoside Hydrogenphosphonates. Effect of a Vicinal Hydroxyl Function on the Stability of H-Phosphonate Diester Bond

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