Improved Synthesis Strategy for N‐Methoxy‐1,3‐Oxazinane Nucleic Acids (MOANAs)

Dependence of the hydrolysis price of a collection of N -methoxy-2-phenyl-1,3-oxazinanes on the Hammett substituent regular of the substituent of the phenyl ring was identified, yielding a response frequent ρ = -1.40 ± .05. Centered on this information and facts, 4-(benzoyloxy)benzaldehyde was selected as a guarding team for a new (2 R ,3 S )-4-(methoxyamino)butane-1,2,3-triol phosphoramidite creating block. The yield of the planning of this setting up block as perfectly as its coupling in automatic oligonucleotide synthesis were being drastically improved when compared to the method documented formerly. The 2-[4-(benzoyloxy)phenyl]-1,3-oxazine security persisted in the course of the synthesis of quick oligonucleotides but was promptly eliminated when the oligonucleotides ended up produced from reliable aid and dissolved in drinking water.

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