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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geprüft am 03.05.2024