Synthesis of 5-aza-7-deazapurine and 3,7-dideazapurine 2'-deoxyribofuranosides by solid-liquid phase-transfer glycosylation.
The 2'-deoxyguanosine isostere 1 as well as the pyrrolo [3,2-c] pyridine 2'-deoxyribofuranosides 2a,b and 3a-d have been synthesized in high yield by solid-liquid phase-transfer glycosylation. It was shown that only the strongly nucleophilic pyrrolo [3,2-c] pyridines formed exclusively beta-2'-deoxyribofuranosides, whereas weakly nucleophilic imidazo [1,2-a]-s-triazines gave mixtures of anomers.
Laboratorium für Organische und Bioorganische Chemie, Universität Osnabrück, FRG.
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F
Seela
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H
Rosemeyer
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W
Bourgeois
D055598:Chemical Phenomena; D002621:Chemistry; D003853:Deoxyribonucleosides / Q000138:chemical synthesis*; D006027:Glycosides; D007202:Indicators and Reagents; D011684:Purine Nucleosides / Q000138:chemical synthesis*
D003853:Deoxyribonucleosides; D006027:Glycosides; D007202:Indicators and Reagents; D011684:Purine Nucleosides