חיפוש מתקדם
Organic Letters
Albert, M., Institut für Organische Chemie, Technische Universität Graz, A-8010 Graz, Austria
De Souza, D., Institut für Organische Chemie, Technische Universität Graz, A-8010 Graz, Austria
Feiertag, P., Institut für Organische Chemie, Technische Universität Graz, A-8010 Graz, Austria
Hönig, H., Institut für Organische Chemie, Technische Universität Graz, A-8010 Graz, Austria
equation presented 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 derivatives in high optical purity. This is exemplified by the synthesis of β-D- and β-L-3′-deoxythymidine.
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תנאי שימוש
A new concept for the preparation of β-L- and β-D-2′,3′-dideoxynucleoside analogues
4
Albert, M., Institut für Organische Chemie, Technische Universität Graz, A-8010 Graz, Austria
De Souza, D., Institut für Organische Chemie, Technische Universität Graz, A-8010 Graz, Austria
Feiertag, P., Institut für Organische Chemie, Technische Universität Graz, A-8010 Graz, Austria
Hönig, H., Institut für Organische Chemie, Technische Universität Graz, A-8010 Graz, Austria
A new concept for the preparation of β-L- and β-D-2′,3′-dideoxynucleoside analogues
equation presented 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 derivatives in high optical purity. This is exemplified by the synthesis of β-D- and β-L-3′-deoxythymidine.
Scientific Publication
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