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Synthesis 2004(8): 1203-1210
DOI: 10.1055/s-2004-822382
DOI: 10.1055/s-2004-822382
PAPER
© Georg Thieme Verlag Stuttgart · New York
Regioselective Syntheses of 7-Halogenated 7-Deazapurine Nucleosides Related to 2-Amino-7-deaza-2′-deoxyadenosine and 7-Deaza-2′-deoxyisoguanosine
Further Information
Received
30 January 2004
Publication Date:
19 May 2004 (online)
Publication History
Publication Date:
19 May 2004 (online)
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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