A New Concept for the Preparation of β-l-and β-d-2', 3'-Dideoxynucleoside Analogues

M Albert, D De Souza, P Feiertag, H Hönig

Index: Albert, Martin; De Souza, Dominic; Feiertag, Petra; Hoenig, Helmut Organic letters, 2002 , vol. 4, # 19 p. 3251 - 3254

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Citation Number: 15

Abstract

A new method for the synthesis of 2', 3'-dideoxynucleoside analogues has been developed. An electrochemical activation of 2-substituted furans is followed by the coupling with a pyrimidine or purine base. This gives planar furyl nucleosides as key intermediates, which are hydrogenated cis-selectively to give the corresponding β-2', 3'-dideoxynucleosides as racemic mixtures. An enzymatic kinetic resolution gives rise to β-d-and β-l-configured ...