Collect. Czech. Chem. Commun.
2011, 76, 1413-1431
https://doi.org/10.1135/cccc2011124
Published online 2011-11-30 18:56:19
7-Halogenated 7-deazapurine 2′-C-methylribonucleosides
Frank Seelaa,b,*, Simone Budowb, Kuiying Xub, Xioahua Pengb and Henning Eickmeierc
a Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany
b Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149 Münster, Germany
c Anorganische Chemie II, Institut für Chemie, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany
Abstract
7-Halogenated 7-deazapurine 2′-C-methylribonucleosides related to adenosine, inosine and guanosine were synthesized employing a “one-pot” glycosylation protocol (Vorbrüggen glycosylation). The immunosine 2′-C-methylribonucleoside 4 was prepared by the same glycosylation strategy. By this route, the synthesis of the anti-HCV active compound 7-fluoro-7-deaza-2′-C-methyladenosine (1b) was notably simplified, while other nucleosides were synthesized for the first time. A single-crystal X-ray analysis of 7-fluoro-7-deaza-2′-C-methylinosine (2b) was performed showing that the glycosylic bond adopts an anti orientation (χ = –139.9(2)°), while the sugar moiety has an N conformation (C3′-endo; P = 4.3(1)°, τm = 42.4(1)°).
Keywords: Nucleosides; 2′-C-Methylribonucleosides; 7-Deazapurines; Pyrrolo[2,3-d]pyrimidine; Glycosylation; Single-crystal X-ray analysis.
References: 34 live references.
