𝔖 Bobbio Scriptorium
✦   LIBER   ✦

8-Aza-2′-deoxyguanosine and Related 1,2,3-Triazolo[4,5-d]pyrimidine 2′-Deoxyribofuranosides

✍ Scribed by Frank Seela; Sigrid Lampe

Publisher
John Wiley and Sons
Year
1993
Tongue
German
Weight
562 KB
Volume
76
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The synthesis of 8‐azaguanine N^9^‐, N^8^‐, and N^7^‐(2′‐deoxyribonucleosides) 1–3, related to 2′‐deoxyguanosine (4), is described. Glycosylation of the anion of 5‐amino‐7‐methoxy‐3__H__‐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, ^13^C‐NMR, and ^1^H‐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 N^7^‐ and N^8^‐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).

📜 SIMILAR VOLUMES

1,2,3-Triazolo[4,5-e]-1,2,4-triazolo[3,4
1,2,3-Triazolo[4,5-e]-1,2,4-triazolo[3,4-c]pyrimidines
✍ Giuliana Biagi; Irene Giorgi; Oreste Livi; Clementina Manera; Valerio Scartoni 📂 Article 📅 1999 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 301 KB 👁 1 views

## Abstract Some new 1,2,3‐triazolo[4,5‐__e__]‐1,2,4‐triazolo[3,4‐__c__]pyrimidmes were prepared starting from the corresponding 1,2,3‐triazolo[4,5‐__d__]pyrimidines __via__ the formation of the 1,2,4‐triazole ring. Thus suitable hydrazino derivatives 6 were condensed with triethyl orthoformate, tr