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Synthesis of 6‐Substituted 1‐Deazapurine 2′‐Deoxyribonucleosides
Author(s) -
Wenzel Thomas,
Seela Frank
Publication year - 1996
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19960790117
Subject(s) - chemistry , deoxyribonucleosides , structural isomer , glycosylation , pyridine , stereochemistry , nuclear magnetic resonance spectroscopy , fluorine 19 nmr , chemical shift , organic chemistry , biochemistry , enzyme
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.