Synthesis of iso-C-nucleoside analogues from 1-(methyl 2-O-benzyl-4,6-O- benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-ones

dc.bibliographicCitation.firstPage1175eng
dc.bibliographicCitation.issue11eng
dc.bibliographicCitation.journalTitleZeitschrift für Naturforschung - Section B Journal of Chemical Scienceseng
dc.bibliographicCitation.volume60eng
dc.contributor.authorOtero, I.
dc.contributor.authorFeist, H.
dc.contributor.authorMichalik, D.
dc.contributor.authorMichalik, M.
dc.contributor.authorQuincoces, J.
dc.contributor.authorPeseke, K.
dc.date.accessioned2020-08-07T13:48:30Z
dc.date.available2020-08-07T13:48:30Z
dc.date.issued2005
dc.description.abstract1-(Methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-altropyranosid-3- yl)but-3-yn-2-one (3a) reacted with 3-amino-1H-1,2,4-triazole and 5-aminopyrazole-4-carboxylic acid derivatives in the presence of base to furnish the triazolo[1,5-a]pyrimidine (5) and the pyrazolo[1,5-a]pyrimidines (8a-d), respectively. Treatment of 1-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy- α-D-altropyranosid-3-yl)-4-phenyl-but-3-yn-2-one (3b) with cyanacetamide, 2-cyano-N-(4-methoxyphenyl)acetamide und N-aryl-3-oxo-butyramides afforded the substituted nicotinonitriles (11a-d). Furthermore, reaction of 3b with 2-benzimidazolyl-acetonitrile yielded the benz[4,5]imidazo[1,2-a]pyridine-4- carbonitrile (13). Deprotection of 8d in two steps afforded the 2-amino-N-benzyl-5-(methyl 3-deoxy-α-D-altropyranosid-3-yl-methyl) pyrazolo[1,5-a]pyrimidine-3-carboxamide (10). Compounds 5 and 11d were treated with AcOH/H2O to furnish the 5-(methyl 2-O-benzyl-3-deoxy-α-D- altropyranosid-3-yl-methyl)[1,2,4]triazolo[1,5-a]pyrimidine (6) and the 3-acetyl-1,2-dihydro-1-(4-methoxyphenyl)-6-(methyl 2-O-benzyl-3-deoxy-α-D- altropyranosid-3-yl-methyl)-4-phenylpyridin-2-one (12), respectively.eng
dc.description.versionpublishedVersioneng
dc.identifier.urihttps://doi.org/10.34657/4022
dc.identifier.urihttps://oa.tib.eu/renate/handle/123456789/5393
dc.language.isoengeng
dc.publisherBerlin : Walter de Gruytereng
dc.relation.doihttps://doi.org/10.1515/znb-2005-1110
dc.relation.issn0932-0776
dc.rights.licenseCC BY-NC-ND 3.0 Unportedeng
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/3.0/eng
dc.subject.ddc540eng
dc.subject.other1,2-Dihydropyridin-2-oneeng
dc.subject.otherBenz[4,5]imidazo[1,2-a]pyridineeng
dc.subject.otherC-Nucleoside Analogueseng
dc.subject.otherGlycosylalkynoneeng
dc.subject.otherPyrazolo[1,5-a]pyrimidineeng
dc.titleSynthesis of iso-C-nucleoside analogues from 1-(methyl 2-O-benzyl-4,6-O- benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-oneseng
dc.typeArticleeng
dc.typeTexteng
tib.accessRightsopenAccesseng
wgl.contributorLIKATeng
wgl.subjectChemieeng
wgl.typeZeitschriftenartikeleng
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