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

Autor(en): Seela, Frank
Budow, Simone
Xu, Kuiying
Peng, Xioahua
Eickmeier, Henning
Stichwörter: 2 `-C-Methylribonucleosides; 7-Deazapurines; 7-THIA-8-OXOGUANOSINE; ANALOGS; ANTIVIRAL ACTIVITY; Chemistry; Chemistry, Multidisciplinary; DERIVATIVES; Glycosylation; HEPATITIS-C; INHIBITORS; NUCLEOSIDES; Pyrrolo[2,3-d]pyrimidine; RIBONUCLEOSIDES; Single-crystal X-ray analysis; THIAZOLO<4,5-D>PYRIMIDINE; VIRUS-RNA REPLICATION
Erscheinungsdatum: 2011
Herausgeber: INST ORGANIC CHEM AND BIOCHEM
Journal: COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
Volumen: 76
Ausgabe: 12
Startseite: 1413
Seitenende: 1431
Zusammenfassung: 
7-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).
ISSN: 00100765
DOI: 10.1135/cccc2011124

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