Reaction of l-halogenoses with nitrogen nucleophiles in the presence of tert-amine. Synthesis of 2'-deoxyribofuranosyl and arabinofuranosyl pyrimidines.
Selective introduction of 2'-deoxyribofuranosyl and arabinofuranosyl moieties onto one of two nitrogen atoms in the pyrimidine ring was demonstrated by the reaction of 1-glycosyl chlorides with pyrimidines protected by the (octylthio)carbonyl group in the presence of tert-amine. Replacing pyrimidines by imidazole derivatives such as benzimidazole and theophylline as nucleophiles gave no nucleosides but orthoamide derivatives.
D000588:Amines; D006219:Halogens; D007202:Indicators and Reagents; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D011743:Pyrimidines / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D000588:Amines; D006219:Halogens; D007202:Indicators and Reagents; D011741:Pyrimidine Nucleosides; D011743:Pyrimidines