7-substituted 8-aza-7-deazapurines and 2,8-diaza-7-deaza-purines: Synthesis of nucleosides and oligonucleotides

Autor(en): Lin, WQ
Xu, KY
Seela, F
Stichwörter: 7-substituted 8-aza-7-deazaadenosine; Biochemistry & Molecular Biology; glycosylation; phosphoramidite; Sonogashira cross coupling
Erscheinungsdatum: 2005
Herausgeber: TAYLOR & FRANCIS INC
Journal: NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
Volumen: 24
Ausgabe: 5-7, SI
Startseite: 869
Seitenende: 873
Zusammenfassung: 
7-Substituted 8-aza-7-deazaadenosines la-e were synthesized by Sonogashira cross coupling from the corresponding 7-iodo nucleoside in 36- 79% yields. Starting from 7-bromo (or 7-iodo)-8-aza- 7-deazaadenine, 2a,b were obtained by acid-catalyzed glycosylation followed by deprotection in 53 and 35% yields, respectively. Compounds 2b was applied to cross coupling reaction to give 2c-d in 34-95% yield. Compounds 2a and 4b were further transformed to the phosphoramidites 5 and 6b in 9 and 49% overall yields, which were incorporated into oligonucleotides.
Beschreibung: 
16th International Roundtable of the International-Society-for-Nucleosides-Nucleotides-and-Nucleic-Acids (IS3NA), Univ Minnesota, Ctr Drug Design, Minneapolis, MN, SEP 12-16, 2004
ISSN: 15257770
DOI: 10.1081/NCN-200059218

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