A new concept for the preparation of beta-L- and beta-D-2',3'-dideoxynucleoside analogues |
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Authors: | Albert Martin De Souza Dominic Feiertag Petra Hönig Helmut |
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Affiliation: | Institut für Organische Chemie, Technische Universit?t Graz, A-8010 Graz, Austria. albert@orgc.tu-graz.ac.at |
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Abstract: | [reaction: see text] 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 beta-2',3'-dideoxynucleosides as racemic mixtures. An enzymatic kinetic resolution gives rise to beta-D- and beta-L-configured derivatives in high optical purity. This is exemplified by the synthesis of beta-D- and beta-L-3'-deoxythymidine. |
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