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

The reaction o f 5'-CMP with methyl, ethyl, «-propyl and isopropyl iodides gave predomi­ nantly ribose alkylated products. Various alkylated derivatives have been characterized using UV spectroscopy, paper electrophoresis, 'H N M R and FAB (negative) mass spectroscopic techniques. Under strongly alkaline conditions the 2'-0-alkylated derivatives are synthesized in maximal yields. Isopropylation reaction gave only a small yield o f the 3'-0-isopropyl deriva­ tive, this could be explained on the basis o f steric hindrance offered to the bulky isopropyl group at the 2'-OH position by the heterocyclic base o f the nucleotide.