Studies on transfer ribonucleic acids and related compounds. VIII(1). Further studies on aromatic phosphoramidates as a protecting group for phosphomonoesters

Abstract

Stability of aromatic phosphoramidates was studied using 2′, 3′-O-di-benzoyluridine5′-phosphoramidates and N,2′,3′-O-tribenzoylcytidine 5′-phosphate. The effect of dicyclohexylcarbodiimide in this mixture was investigated. Deconposition of the anilidate was slower in the presence of DCC. Substituted anilidates of uridine 5′-phosphate were synthesized and the stability of these amidates in anhydrous pyridine was studied. 2′-O-Benzoyluridine 3′-phosphoranilidate and the corresponding β-naphthylidatewere conpared in their stabilities in anhydrous pyridine, 50% aqueouspyridine and 80% acetic acid. 2′-O-Benzoyluridine 3′-phosphoro-β-naphthylidate was used for synthesis of dinucleotides.