Regioselective Syntheses of 7-Halogenated 7-Deazapurine Nucleosides Related to 2-Amino-7-deaza-2′-deoxyadenosine and 7-Deaza-2′-deoxyisoguanosine
- 19 May 2004
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 2004 (08) , 1203-1210
- https://doi.org/10.1055/s-2004-822382
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.Keywords
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