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A new concept for the preparation of β-L- and β-D-2′,3′-dideoxynucleoside analogues
Year:
2002
Source of publication :
Organic Letters
Authors :
Hönig, Helmut
;
.
Volume :
4
Co-Authors:
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
Facilitators :
From page:
3251
To page:
3254
(
Total pages:
4
)
Abstract:
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.
Note:
Related Files :
chemistry
Models, Molecular
Molecular structure
Synthesis
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More details
DOI :
10.1021/ol026460+
Article number:
Affiliations:
Database:
Scopus
Publication Type:
article
;
.
Language:
English
Editors' remarks:
ID:
24542
Last updated date:
02/03/2022 17:27
Creation date:
17/04/2018 00:08
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Scientific Publication
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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