Regioselective syntheses of 7-halogenated 7-deazapurine nucleosides related to 2-amino-7-deaza-2 `-deoxyadenosine and 7-deaza-2 `-deoxyisoguanosine

Autor(en): Seela, F
Peng, XH
Stichwörter: ACID RELATED-COMPOUNDS; ANALOGS; ANTIVIRAL ACTIVITY; Chemistry; Chemistry, Organic; CONFORMATIONAL-ANALYSIS; glycosylations; halogenation; nucleosides; OLIGONUCLEOTIDE DUPLEXES; PHASE-TRANSFER GLYCOSYLATION; PYRROLO<2,3-D>PYRIMIDINE NUCLEOSIDES; pyrrolo[2,3-d]pyrimidines; PYRROLOPYRIMIDINE NUCLEOSIDES; regioselectivity; SUGAR CONFORMATION; TUBERCIDIN
Erscheinungsdatum: 2004
Herausgeber: GEORG THIEME VERLAG KG
Journal: SYNTHESIS-STUTTGART
Ausgabe: 8
Startseite: 1203
Seitenende: 1210
Zusammenfassung: 
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 H-1,H-1 NMR coupling constants.
ISSN: 00397881
DOI: 10.1055/s-2004-822382

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