8-AZAGUANINE 2',3'-DIDEOXYRIBONUCLEOSIDES - GLYCOSYLATION OF THE 5-AMINO-7-METHOXY-3H-1,2,3-TRIAZOLO[4,5-D]PYRIMIDINYL ANION WITH 2,3-DIDEOXY-D-GLYCERO-PENTOFURANOSYL CHLORIDE

DC FieldValueLanguage
dc.contributor.authorSEELA, F
dc.contributor.authorMERSMANN, K
dc.date.accessioned2021-12-23T15:59:06Z-
dc.date.available2021-12-23T15:59:06Z-
dc.date.issued1993
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/3737-
dc.description.abstractThe synthesis of the regioisomeric 8-azaguanine N7-, N8-, and N-9-(beta-D-2',3'-dideoxyribonucleosides) (1, 2, and 3, respectively) and of the diamino derivative 13 is described. The anion of 5-amino-7-methoxy-3H-1,2,3-tri-azolo[4,5-d]pyrimidine (5) was glycosylated with 5-O-[(tert-butyl)dimethylsilyl]-2,3-dideoxy-D-glycero-pentofuranosyl chloride (6; anomeric mixture), yielding the regioisomeric 2',3'-dideoxyribofuranosides as anomeric mixtures 7a/10a, 8a/11a, and 9a/12a. They were desilylated with Bu4NF in THF affording the 5-amino-7-methoxy-nucleosides 7b-12b. Treatment with aqueous NaOH gave the beta-azaguanine beta-D-2',3'-dideoxynucleosides 1-3 and their alpha-D-anomers 14-16. The reaction of 7b with NH3/MeOH yielded the diamino compound 13. The N-glycosylic bond of 8-aza-2',3'-dideoxyguanosine (1) is four-times more stable against acid than that of 2',3'-dideoxyguanosine. Compounds 1, 2, and 13 were converted to their 5'-triphosphates 17-19 which showed only modest inhibitory activity against HIV-reverse transcriptase.
dc.language.isoen
dc.publisherNEW SWISS CHEMICAL SOC
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subject8-AZAPURINES
dc.subjectACID
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectNUCLEOBASE ANION
dc.subjectNUCLEOSIDES
dc.title8-AZAGUANINE 2',3'-DIDEOXYRIBONUCLEOSIDES - GLYCOSYLATION OF THE 5-AMINO-7-METHOXY-3H-1,2,3-TRIAZOLO[4,5-D]PYRIMIDINYL ANION WITH 2,3-DIDEOXY-D-GLYCERO-PENTOFURANOSYL CHLORIDE
dc.typejournal article
dc.identifier.doi10.1002/hlca.19930760603
dc.identifier.isiISI:A1993LZ23600002
dc.description.volume76
dc.description.issue6
dc.description.startpage2184
dc.description.endpage2193
dc.publisher.placeVERLAG HELVETICA CHIMICA ACTA, MALZGASSE 21, POSTFACH 313, CH-4010 BASEL, SWITZERLAND
dcterms.isPartOf.abbreviationHelv. Chim. Acta
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