Studies on tRNA and Related Compounds. XXXVII. Synthesis and Physical Properties of 2′- or 3′-O-(o-Nitrobenzyl)nucleosides: The Use of o-Nitrophenyldiazomethane as a Synthetic Reagent

Abstract

2′- and 3′-O-(o-Nitrobenzyl) derivatives of uridine, cytidine, adenosine and guanosine were synthesized by treatment of uridine, N-benzoylcytidine, N-benzoyladenosine and N-isobutyrylguanosine, respectively, with o-nitrophenyldiazomethane followed by isolation and deblocking. 3′-O-(o-Nitrobenzyl)guanosine is a novel compound. By using N-acylated nucleosides, separation of the 2′- and 3′-substituted isomers on silica gel became feasible and these compounds were useful intermediates for the synthesis of oligoribonucleo-tides. Some physical properties of these compounds were studied by ultraviolet, nuclear magnetic resonance, circular dichroism and the 2′-substituted isomers were found to have more stacked structures than the 3′-isomers. © 1981, The Pharmaceutical Society of Japan. All rights reserved.