Synthesis of 7-halogenated 8-aza-7-deaza-2 `-deoxyguanosines and related pyrazolo[3,4-d]pyrimidine 2 `-deoxyribonucleosides

DC FieldValueLanguage
dc.contributor.authorSeela, F
dc.contributor.authorBecher, G
dc.date.accessioned2021-12-23T16:04:51Z-
dc.date.available2021-12-23T16:04:51Z-
dc.date.issued1998
dc.identifier.issn00397881
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/6636-
dc.description.abstractThe synthesis of 7-bromo and 7-iodo derivatives of 8-aza-7-deaza-2'-deoxyguanosine (2, 3) as well as the halogenated 4-alkoxy derivatives 4a-c and 5a-c is described. Glycosylation of the halogenated pyrazolo[3,4-d]pyrimidine anions of 7a-c or 8a-c with 2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride (9) yields regioisomeric glycosylation products, the N(1)-isomers 10a-c and 11a-c as well as the N(2)-compounds 12a-c. The latter isomers lose their halogen during the glycosylation in the presence of non-anhydrous KOH. Anhydrous conditions (NaH) furnished 10c, 11c together with the halogenated N(2)-isomers 13a,b. Compounds 10a-c, and 11a-c were deprotected and converted to the 4-alkoxy nucleosides 4a-c and 5a-c. The N(1)-nucleosides 4c and 5c were hydrolyzed to give the 7-bromo or 7-iodo derivatives of 8-aza-7-deaza-2'-deoxyguanosines 2 and 3. Different from regular 2'-deoxyribonucleosides the sugar moiety of pyrazolo[3,4-d]pyrimidine 2'-deoxyribonucleosides shows a preferred N-type pucker (T-3(2)) in solution a conformation which is also detected in the solid state.
dc.language.isoen
dc.publisherGEORG THIEME VERLAG
dc.relation.ispartofSYNTHESIS-STUTTGART
dc.subject2'-DEOXYRIBOFURANOSIDES
dc.subject7-DEAZA-2'-DEOXYGUANOSINE
dc.subject7-DEAZAPURINE DNA
dc.subjectBASE
dc.subjectBIOLOGICAL-ACTIVITY
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectglycosylation
dc.subjecthalogenation
dc.subjectNUCLEOSIDES
dc.subjectOLIGONUCLEOTIDES
dc.subjectPHASE-TRANSFER GLYCOSYLATION
dc.subjectpyrazolo[3,4-d]pyrimidines
dc.subjectSTABILITY
dc.subjectsugar conformation
dc.titleSynthesis of 7-halogenated 8-aza-7-deaza-2 `-deoxyguanosines and related pyrazolo[3,4-d]pyrimidine 2 `-deoxyribonucleosides
dc.typejournal article
dc.identifier.isiISI:000072542200016
dc.description.issue2
dc.description.startpage207
dc.description.endpage214
dc.publisher.placeP O BOX 30 11 20, D-70451 STUTTGART, GERMANY
dcterms.isPartOf.abbreviationSynthesis
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