7-HALOGENATED 7-DEAZAPURINE 2 `-C-METHYLRIBONUCLEOSIDES

DC FieldValueLanguage
dc.contributor.authorSeela, Frank
dc.contributor.authorBudow, Simone
dc.contributor.authorXu, Kuiying
dc.contributor.authorPeng, Xioahua
dc.contributor.authorEickmeier, Henning
dc.date.accessioned2021-12-23T16:05:51Z-
dc.date.available2021-12-23T16:05:51Z-
dc.date.issued2011
dc.identifier.issn00100765
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/7245-
dc.description.abstract7-Halogenated 7-deazapurine 2'-C-methylribonucleosides related to adenosine, inosine and guanosine were synthesized employing a ``one-pot'' glycosylation protocol (Vorbruggen glycosylation). The immunosine 2'-C-methylribonucleoside 4 was prepared by the same glycosylation strategy. By this route, the synthesis of the anti-HCV active compound 7-fluoro-7-deaza-2'-C-methyladenosine (1b) was notably simplified, while other nucleosides were synthesized for the first time. A single-crystal X-ray analysis of 7-fluoro-7-deaza-2'-C-methylinosine (2b) was performed showing that the glycosylic bond adopts an anti orientation (chi = -139.9(2)degrees), while the sugar moiety has an N conformation (C3'-endo; P = 4.3(1)degrees, tau(m) = 42.4(1)degrees).
dc.description.sponsorshipChemBiotech, Munster, Germany; We would like to thank Dr. P. Leonard for helpful discussions and support. We are grateful for critical reading of the manuscript by Mr. S. S. Pujari. Financial support from ChemBiotech, Munster, Germany is highly appreciated.
dc.language.isoen
dc.publisherINST ORGANIC CHEM AND BIOCHEM
dc.relation.ispartofCOLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
dc.subject2 `-C-Methylribonucleosides
dc.subject7-Deazapurines
dc.subject7-THIA-8-OXOGUANOSINE
dc.subjectANALOGS
dc.subjectANTIVIRAL ACTIVITY
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectDERIVATIVES
dc.subjectGlycosylation
dc.subjectHEPATITIS-C
dc.subjectINHIBITORS
dc.subjectNUCLEOSIDES
dc.subjectPyrrolo[2,3-d]pyrimidine
dc.subjectRIBONUCLEOSIDES
dc.subjectSingle-crystal X-ray analysis
dc.subjectTHIAZOLO<4,5-D>PYRIMIDINE
dc.subjectVIRUS-RNA REPLICATION
dc.title7-HALOGENATED 7-DEAZAPURINE 2 `-C-METHYLRIBONUCLEOSIDES
dc.typejournal article
dc.identifier.doi10.1135/cccc2011124
dc.identifier.isiISI:000299816100002
dc.description.volume76
dc.description.issue12
dc.description.startpage1413
dc.description.endpage1431
dc.publisher.placeACAD SCI CZECH REPUBLIC, FLEMINGOVO NAM 2, PRAGUE 6 166 10, CZECH REPUBLIC
dcterms.isPartOf.abbreviationCollect. Czech. Chem. Commun.
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