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Abstract
Oxidation-reduction condensation using triphenylphosphine and 2,2′-dipyridildisulfide was carried out for forming a phosphodiester bond between a mono-anionic thymidine 3′-Hphosphonate derivative and 3′-O-acetylthymidine. This reaction proceeded with simultaneous coupling and oxidation. The detailed NMR analysis of this reaction shows that an S-(2-pyridyl) phosphorothioate diester derivative was formed as an initial intermediate.
Highlights
For internucleotidic bond formation in oligonucleotide synthesis,[1] the H-phosphonate method[2] has been used along with the more popular phosphoramidite method.[3]
When compound 1 was allowed to react with compound 2 in the presence of 5.0 equiv of PPh3 and 10.0 equiv of PySSPy in dry pyridine at room temperature for 12 h, DMTrTpToAc 4 was obtained in 88% yield
To clarify the oxidative condensation reaction mechanism, we studied the time-course analysis of the products by 31P NMR spectroscopy (Figure 2)
Summary
For internucleotidic bond formation in oligonucleotide synthesis,[1] the H-phosphonate method[2] has been used along with the more popular phosphoramidite method.[3]. When compound 1 was allowed to react with compound 2 in the presence of 5.0 equiv of PPh3 and 10.0 equiv of PySSPy in dry pyridine at room temperature for 12 h, DMTrTpToAc 4 was obtained in 88% yield.
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