Regioselectivity of the Mannich reaction on pyrrolo[2,3-d]pyrimidine nucleosides related to 7-deaza-2'-deoxyadenosine or 7-deaza-2'-deoxyguanosine

Autor(en): Seela, F
Chen, YM
Zulauf, M
Stichwörter: ANALOGS; Chemistry; Chemistry, Organic; Mannich reaction; nucleosides; PHASE-TRANSFER GLYCOSYLATION; pyrrolo[2,3-d]pyrimidines; queuosine; regioselectivity
Erscheinungsdatum: 1997
Herausgeber: GEORG THIEME VERLAG
Journal: SYNTHESIS-STUTTGART
Ausgabe: 9
Startseite: 1067-&
Zusammenfassung: 
Mannich reactions were performed on 7-deazapurine 2'-deoxyribonucleosides and the regioselectivity was studied. 7-Deaza-2'-deoxyadenosine (2'-deoxytubercidin, 4a) furnished the 7-substituted Mannich base 5a. The side chain was introduced in the 8-position when 7-deaza-2 `-deoxyguanosine was used (Mannich base 7a). The regioselectivity changed back from position 8 to 7 when the reaction was performed on 4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine 2'-deoxyribonucleoside (12). Thus a 7-substituted Mannich product of 7-deaza-2 `-deoxyguanosine could be obtained after demethylation and oxidation of the methylthio group followed by displacement of the oxidized 2-substituent with ammonia.
ISSN: 00397881

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