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Synthesis of 3-Deaza-2′-deoxyadenosine and 3-Deaza-2′,3′-dideoxyadenosine: Glycosylation of the 4-Chloroimidazo[4,5-c]pyridinyl Anion

✍ Scribed by Frank Seela; Helmut Rosemeyer; Sabine Fischer

Book ID
102858285
Publisher
John Wiley and Sons
Year
1990
Tongue
German
Weight
589 KB
Volume
73
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The convergent syntheses of 3‐deazapurine 2′‐deoxy‐β‐D‐ribonucleosides and 2′,3′‐dideoxy‐D‐ribonucleosides, including 3‐deaza‐2′‐deoxyadenosine (1a) and 3‐deaza‐2′,3′‐dideoxyadenosine (1b) is described. The 4‐chloro‐l__H__‐imidazo[4,5‐c]pyridinyl anion derived from 5 was reacted with either 2′‐deoxyhalogenose 6 or 2′,3′‐dideoxyhalogenose 10 yielding two regioisomeric (N^1^ and N^3^) glycosylation products. They were deprotected and converted into 4‐substituted imidazo[4,5‐c]pyridine 2′‐deoxy‐β‐D‐ribonucleosides and 2′,3′‐dideoxy‐D‐ribonucleosides. Compounds 1a and 1b proved to be more stable against proton‐catalyzed N‐glycosylic bond hydrolysis than the parent purine nucleosides and were not deaminated by adenosine deaminase.

📜 SIMILAR VOLUMES

3-Deaza-2′-deoxyadenosine: Synthesis via
3-Deaza-2′-deoxyadenosine: Synthesis via 4-(methylthio)-1H-imidazo[4,5-c]pyridine 2′-deoxyribonucleosides and properties of oligonucleotides
✍ Frank Seela; Thomas Grein; Samuel Samnick 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 German ⚖ 654 KB

## Abstract The synthesis of 4‐(methylthio)‐1__H__‐imidazo[4,5‐__c__]pyridine 2′‐deoxy‐β‐D‐ribonucleosides 2 and 9 and the conversion of the __N__^1^‐isomer 2 into the 2′,3′‐didehydro‐2′,3′‐dideoxyribonucleoside 3a or (__via__ 7) 3‐deaza‐2′‐deoxyadenosine (1) is described. Phosphonate building bloc