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

DC FieldValueLanguage
dc.contributor.authorSeela, F
dc.contributor.authorChen, YM
dc.contributor.authorZulauf, M
dc.date.accessioned2021-12-23T16:02:30Z-
dc.date.available2021-12-23T16:02:30Z-
dc.date.issued1997
dc.identifier.issn00397881
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/5452-
dc.description.abstractMannich 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.
dc.language.isoen
dc.publisherGEORG THIEME VERLAG
dc.relation.ispartofSYNTHESIS-STUTTGART
dc.subjectANALOGS
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectMannich reaction
dc.subjectnucleosides
dc.subjectPHASE-TRANSFER GLYCOSYLATION
dc.subjectpyrrolo[2,3-d]pyrimidines
dc.subjectqueuosine
dc.subjectregioselectivity
dc.titleRegioselectivity of the Mannich reaction on pyrrolo[2,3-d]pyrimidine nucleosides related to 7-deaza-2'-deoxyadenosine or 7-deaza-2'-deoxyguanosine
dc.typejournal article
dc.identifier.isiISI:A1997YB90300014
dc.description.issue9
dc.description.startpage1067-&
dc.publisher.placeP O BOX 30 11 20, D-70451 STUTTGART, GERMANY
dcterms.isPartOf.abbreviationSynthesis
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