ArticleThe Journal of organic chemistry2026
Stereocontrolled Synthesis of Dimethylamino Phosphorochloridate Monomers toward Stereopure Phosphorodiamidate Morpholino Oligonucleotides.
Article in The Journal of organic chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
As antisense oligonucleotides, phosphorodiamidate morpholino oligonucleotides (PMOs) exhibit excellent properties. However, they possess two stereoisomers for each phosphorus atom, and these stereoisomers exhibit different physicochemical and biological properties. In this study, we developed a stereocontrolled synthesis method of dimethylamino phosphorochloridate monomers, which was used for a practical synthesis method of PMOs, from oxazaphospholidine derivatives. However, the condensation of a 5'-oxazaphospholidine derivative with an amine under acidic conditions is challenging because the resulting phosphoramidite intermediate can be activated under such conditions. To address this challenge, in the proposed synthesis method, a morpholino nucleoside 5'-oxazaphospholidine derivative was condensed with a phenol derivative with a low p
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