STEREOSELECTIVE SYNTHESIS OF INDAZOLE 2'-DEOXY-BETA-D-RIBONUCLEOSIDES - GLYCOSYLATION OF THE NUCLEOBASE ANION

DC FieldValueLanguage
dc.contributor.authorSEELA, F
dc.contributor.authorBOURGEOIS, W
dc.date.accessioned2021-12-23T15:59:53Z-
dc.date.available2021-12-23T15:59:53Z-
dc.date.issued1991
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/4200-
dc.description.abstractThe glycosylation of indazolyl anions derived from 4a, b with 2-deoxy-3,5-bis-O-(4-methylbenzoyl)-alpha-D-erythro-pentofuranosyl chloride (5) is described. The reaction was stereoselective - exclusive beta-D-anomer formation - but regioisomeric N1-and N2-(2'-deoxy-beta-D-ribofuranosides) (i.e. 6a and 7a, resp., and 6b and 7b, resp.) were formed in about equal amounts. They were deprotected to yield 8a, b and 9a, b. Compound 1, related to 2'-deoxyadenosine (3), and its regioisomer 2 were obtained from 8b and 9b, respectively, by catalytic hydrogenation. The anomeric configuration as well as the position of glycosylation were determined by 1D NOE-difference spectroscopy. The first protonation site of 1 and 2 was found to be the NH2 group. The N-glycosylic bond of H-1-indazole N1-(2'-deoxyribofuranosides) is more stable than that of the parent purine nucleosides. Compound 1 is no substrate for adenosine deaminase.
dc.language.isoen
dc.publisherNEW SWISS CHEMICAL SOC
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subject2'-DEOXYRIBOFURANOSIDES
dc.subjectADENINE DINUCLEOTIDES
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectDERIVATIVES
dc.subjectDIFFERENCE
dc.subjectLIQUID
dc.subjectPHASE-TRANSFER GLYCOSYLATION
dc.subjectPYRAZOLO<3,4-D>PYRIMIDINES
dc.titleSTEREOSELECTIVE SYNTHESIS OF INDAZOLE 2'-DEOXY-BETA-D-RIBONUCLEOSIDES - GLYCOSYLATION OF THE NUCLEOBASE ANION
dc.typejournal article
dc.identifier.doi10.1002/hlca.19910740209
dc.identifier.isiISI:A1991FE11500008
dc.description.volume74
dc.description.issue2
dc.description.startpage315
dc.description.endpage322
dc.publisher.placeVERLAG HELVETICA CHIMICA ACTA, MALZGASSE 21, POSTFACH 313, CH-4010 BASEL, SWITZERLAND
dcterms.isPartOf.abbreviationHelv. Chim. Acta
Show simple item record

Page view(s)

2
Last Week
0
Last month
0
checked on Apr 12, 2024

Google ScholarTM

Check

Altmetric