7-iodo-5-aza-7-deazaguanine: Syntheses of anomeric D- and L-configured 2-deoxyribonucleosides

DC FieldValueLanguage
dc.contributor.authorLin, WQ
dc.contributor.authorZhang, XM
dc.contributor.authorSeela, F
dc.date.accessioned2021-12-23T16:03:37Z-
dc.date.available2021-12-23T16:03:37Z-
dc.date.issued2004
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/6093-
dc.description.abstractIodination of N-2-isobutyryl-5-aza-7-deazaguanine (7) with N-iodosuccinimide (NIS) gave 7-iodo-N-2-isobutyryl-5-aza-7-deazaguanine (8) in a regioselective reaction (Scheme 1). Nucleobase-anion glycosylation of 8 with 2-deoxy-3,5-di-O-toluoyl-alpha-D- or alpha-L-erythro-pentofuranosyl chloride furnished anomeric mixtures of D-and L-nucleosides. The anomeric D-nucleosides were separated by crystallization to give the a-D-anomer and beta-D-anomer with excellent optical purity. Deprotection gave the 7-iodo-5-aza-7-deazaguanine 2'-deoxyribonucleosides 3 (beta-D; greater than or equal to 99% de) and 4 (alpha-D; greater than or equal to 99% de). The reaction sequence performed with the D-series was also applied to L-nucleosides to furnish compounds 5 (beta-L; greater than or equal to 99% de) and 6 (alpha-L; greater than or equal to 95% de).
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subject7-IODO
dc.subjectANALOGS
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectDERIVATIVES
dc.subjectDNA
dc.subjectDUPLEX STABILITY
dc.subjectGUANINE
dc.subjectNUCLEOSIDES
dc.subjectOLIGONUCLEOTIDES
dc.subjectPARALLEL
dc.title7-iodo-5-aza-7-deazaguanine: Syntheses of anomeric D- and L-configured 2-deoxyribonucleosides
dc.typejournal article
dc.identifier.doi10.1002/hlca.200490201
dc.identifier.isiISI:000224353800004
dc.description.volume87
dc.description.issue9
dc.description.startpage2235
dc.description.endpage2244
dc.identifier.eissn15222675
dc.publisher.placePOSTFACH 101161, 69451 WEINHEIM, GERMANY
dcterms.isPartOf.abbreviationHelv. Chim. Acta
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