Studies on the Alkylation of 5′-CMP under Alkaline Conditions

Abstract

The reaction of 5′-CMP with methyl, ethyl, n-propyl and isopropyl iodides gave predominantly ribose alkylated products. Various alkylated derivatives have been characterized using UV spectroscopy, paper electrophoresis, 1H NMR and FAB (negative) mass spectroscopic techniques. Under strongly alkaline conditions the 2′-O-alkylated derivatives are synthesized in maximal yields. Isopropylation reaction gave only a small yield of the 3′-O-isopropyl derivative, this could be explained on the basis of steric hindrance offered to the bulky isopropyl group at the 2′-OH position by the heterocyclic base of the nucleotide. Show more