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Synthesis of 6-Substituted 1-Deazapurine 2′-Deoxyribonucleosides

✍ Scribed by Thomas Wenzel; Frank Seela

Publisher
John Wiley and Sons
Year
1996
Tongue
German
Weight
590 KB
Volume
79
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The synthesis of 6‐substituted 1‐deazapurine 2′‐deoxyribonucleosides is described. Glycosylation of the 1‐deazapurine (imidazo[4,5‐b]pyridine) anions with the α‐D‐halogenose 5 gives stereoselectively N^7^‐ and N^9^‐ regioisomers. ^1^H‐NMR NOE and ^13^C‐NMR spectroscopy are used for unambiguous assignment of isomers, and ^15^N‐NMR chemical shifts are correlated with σ~para~ Hammett constants and point charges.

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