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Synthesis of 8-Aza-1,3-dideaza-2′-deoxyadenosine and 5,6-Disubstituted Benzotriazole 2′-Deoxy-β-D-Ribofuranosides via Nucleobase-Anion Glycosylation

✍ Scribed by Zygmunt Kazimierczuk; Frank Seela

Publisher: John Wiley and Sons
Year: 1990
Tongue: German
Weight: 631 KB
Volume: 73
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19900730211

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✦ Synopsis

Abstract

The synthesis of 8‐aza‐1,3‐dideaza‐2′‐deoxyadenosine (3a) as well as of 4‐ and 5,6‐substituted benzotriazole 2′‐deoxy‐β‐D‐ribonucleosides is described (Schemes 1–3). Glycosylation of benzotriazole anions is stereoselective in all cases (exclusive β‐D‐anomer formation), but regioisomeric N^1^, N^2^, and N^3^‐(2′‐deoxyribofuranosides) are formed. The distribution of the regioisomers is controlled by the nucleobase substituents. Anomeric configuration as well as the position of glycosylation are determined by UV and NMR in combination with 1D‐NOE‐difference spectroscopy. The unprotonated forms of 4‐aminobenzotriazoic 2′‐deoxy‐β‐D‐ribofuranosides 3a–c exhibit strong fluorescence.

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