1,N6-Etheno-7-deaza-2,8-diazaadenosine: syntheses, properties and conversion to 7-deaza-2,8-diazaadenosine.
نویسندگان
چکیده
1,N6-Etheno-7-deaza-2,8-diazaadenosine (4) was synthesized from 8-aza-7-deazaadenosine (6) in 64% overall yield. The starting material 6 was obtained by the direct glycosylation of 8-aza-7-deazaadenine (7) with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-d-ribofuranose (8) (NO2 CH3, BF3 x Et2O; 77% yield). Compound 4 was transformed into 7-deaza-2,8-diazaadenosine (5). The fluorescence of compound 4 shows an emission maximum at 531 nm (phosphate buffer; pH 7.0), which is bathochromically shifted compared to 1,N(6)-etheno-2-azaadenosine (3a) (495 nm). A conformational analysis was performed in the solid state and in solution.
منابع مشابه
1,N6-Etheno derivative of 7-deaza-2,8-diazaadenosine.
In the tricyclic nucleoside 7-( -d-ribofuranosyl)-7H-imidazo[1,2-c]pyrazolo[4,3-e][1,2,3]triazine, C11H12N6O4, the conformation of the N-glycosyl bond is intermediate between anti and high anti [ = ÿ103.5 (3) ]. The ribofuranose moiety adopts a 3T 2 sugar pucker (S-type sugar) and the conformation at the exocyclic CÐC bond is ap (gauche±trans). Molecules of the title compound form a three-dimen...
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 3 9 شماره
صفحات -
تاریخ انتشار 2005