Intramolecular thermal reactions of the derivatives of 5′-azido-5′-deoxyuridine. A new feasible route to the regio- and stereospecific synthesis of reversed nucleosides carrying a substituted five-membered heterocycle
| العنوان: | Intramolecular thermal reactions of the derivatives of 5′-azido-5′-deoxyuridine. A new feasible route to the regio- and stereospecific synthesis of reversed nucleosides carrying a substituted five-membered heterocycle |
|---|---|
| المؤلفون: | Tadashi Sasaki, Toshimichi Suzuki, Toyoyuki Sugiura, Katsumaro Minamoto |
| بيانات النشر: | Oxford University Press, 1978. |
| سنة النشر: | 1978 |
| مصطلحات موضوعية: | chemistry.chemical_compound, Stereospecificity, chemistry, Biochemistry, Stereochemistry, Intramolecular force, Organic Chemistry, Genetics, Uracil, Biology, Deoxyuridine, Article |
| الوصف: | With a view to probing the reactivity of the “naked” 5,6-double bond of uracil nucleosides as a dipolarophile, l-(5′-azido-5′-deoxy-2′,3′- O -isopropylidene-ß-D-ribofuranosyl)uracil ( l a) and its analogs l b-d were synthesized and submitted to an intramolecular thermal reaction, which yielded N (l) ,5′-anhydro-Nω-(2′,3′- O -isopropylidene-β-D-ribofuranosyl)-4-allophanoyl-1,2,3-triazole ( 3 a) and its analogs 3 b-c in moderate to high yields with 6,5′-imino cyclouridine derivatives ( 4 ) as minor products. The intermediary cycloadduct 2 was trapped as 9,5′-cyclo-3-(2′,3′-O-isopropylidene-β-D-ribofuranosyl)-8-azaxanthine (5). Compounds 3 c and 3 a were regio- and stereospecifically transformed to 4-methoxy and carboxamido substituted triazole reversed nucleosides 7 a-b and ll a-b. |
| اللغة: | English |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::09fe7a4c9f6ce27aadc655b2a4a1a487 https://europepmc.org/articles/PMC6581332/ |
| Rights: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....09fe7a4c9f6ce27aadc655b2a4a1a487 |
| قاعدة البيانات: | OpenAIRE |
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