Abstract
AbstractThe synthesis of 8‐azaguanine N9‐, N8‐, and N7‐(2′‐deoxyribonucleosides) 1–3, related to 2′‐deoxyguanosine (4), is described. Glycosylation of the anion of 5‐amino‐7‐methoxy‐3H‐1,2,3‐triazolo[4,5‐d]pyrimidine (5) with 2‐deoxy‐3,5‐di‐O‐(4‐toluoyl)‐α‐D‐erythro‐pentofuranosyl chloride (6) afforded the regioisomeric glycosylation products 7a/7b, 8a/8b, and 9 (Scheme 1) which were detoluoylated to give 10a, 10b, 11a, 11b, and 12a. The anomeric configuration as well as the position of glycosylation were determined by combination of UV, 13C‐NMR, and 1H‐NMR NOE‐difference spectroscopy. The 2‐amino‐8‐aza‐2′‐deoxyadenosine (13), obtained from 7a, was deaminated by adenosine deaminase to yield 8‐aza‐2′‐deoxyguanosine (1), whereas the N7‐ and N8‐regioisomers were no substrates of the enzyme. The N‐glycosylic bond of compound 1 (0.1 N HCl) is ca. 10 times more stable than that of 2′‐deoxyguanosine (4).
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