Synthesis and process optimization for a novel phosphorodiamidate morpholinoguanylic monomer
A synthesis route of a novel phosphoramide morpholinoline-oligoguanylate monomer using guanosine as raw ma-terial was developed.Based on the protection of the amino group on the base and 5'-OH in ribose,the ribose ring is converted in-to a morpholine ring to obtain the protected morpholine guanosine.A triphenylmethylation reaction was carried out on the mor-pholine ring and purine 6-O position was modified using the Mitsunobu reaction.N,N-dimethylaminophosphorylation reaction is performed on the deprotected hydroxyl group to synthesize the target product.In this study,the conditions of the Mitsunobu re-action and phosphorylation reaction were optimized.Under optimized conditions,the total yield of the new synthetic route was 14.1％.The structure of intermediate products and target products were characterized by LC-MS,1 H NMR and 31P NMR.
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