A reinvestigated mechanism of ribosylation of adenine under silylating conditions

Article abstract of DOI:10.1016/j.tet.2006.08.046

The mechanism of chemical synthesis of adenosine has been reinvestigated. Depending on the reaction conditions and the presence of N⁶-protecting groups, ribosylation of adenine proceeds via different kinetic products: 3-riboadenine in strongly acidic media, 7-ribosylated derivative in the silyl method, and 1-(β-d-ribofuranosyl)adenine when applying N⁶-acyladenine and silylating conditions.