Regioselective Syntheses of 7-Halogenated 7-Deazapurine Nucleosides Related to 2-Amino-7-deaza-2′-deoxyadenosine and 7-Deaza-2′-deoxyisoguanosine

Frank Seela; Xiaohua Peng

doi:10.1055/s-2004-822382

PAPER

Regioselective Syntheses of 7-Halogenated 7-Deazapurine Nucleosides Related to 2-Amino-7-deaza-2′-deoxyadenosine and 7-Deaza-2′-deoxyisoguanosine

Frank Seela*, Xiaohua Peng
Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastr. 7, 49069 Osnabrück, Germany and , Center for Nanotechnology, Gievenbecker Weg 11, 48149 Münster, Germany
Fax: +49(541)9692370; e-Mail: Frank.Seela@uni-osnabrueck.de;

Abstract

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Abstract

The syntheses of 7-halogenated derivatives 3b-e of 2-amino-7-deaza-2′-deoxyadenosine as well as 7-bromo and 7-chloro-7-deaza-2′-deoxyisoguanosines 4b-c are described. Nucleobase anion glycosylation was employed for the convergent nucleoside synthesis. The regioselective 7-halogenation was performed either on the nucleoside precursor 7 or on the nucleobase 12. Two bromo substituents were introduced in the 7- and 8-position when the unprotected 2-amino nucleoside 9 was used. Conformational analysis of the sugar moiety of nucleosides 3a-e and 4a-c was performed on the basis of vicinal ¹H,¹H NMR coupling constants.

Key words

glycosylations - nucleosides - pyrrolo[2,3-d]pyrimidines - halogenation - regioselectivity - sugar conformation

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