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Relevant academic research and scientific papers

Nucleoside Syntheses XXIII. On the Mechanism of Nucleoside Synthesis

During the silyl-Hilbert-Johnson nucleoside synthesis with Friedel-Crafts catalysts three processes occur simultanously: A) The formation of the electrophilic sugar cation.B) The ?-complex formation between the silylated base and the Friedel-Crafts catalyst and finally C) the reaction of the electrophilic sugar cation with the silylated base to the nucleoside.Mode and rate of ?-complex formation between the silylated base and the Friedel-Crafts catalysts were monitored by 13C-NMR.The probable mechanism of nucleoside synthesis and the factors which influence course and yield of nucleoside synthesis are discussed.A) The formation of the electrophilic sugar cation.B) The ?-complex formation between the silylated base and Friedel-Crafts catalyst and finally C) the reaction of the electrophilic sugar cation with the silylated base to the nucleoside.Mode and rate of the ?-complex formation between the silylated base and the Friedel-Crafts catalysts were monitored by 13C-NMR.The probable mechanism of the nucleoside synthesis and the factors which influence course and yield of nucleoside synthesis are discussed.