Asymmetric Synthesis of a Xanthine Dehydrogenase Inhibitor (S)-(–)-BOF-4272 : Mechanism of Chiral Diaryl Sulfoxide Formation: Phosphorus, Sulfur, and Silicon and the Related Elements: Vol 120, No 1

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Abstract

A pyrazolotriazine derivative (BOF-4272), a potent xanthine dehydrogenase inhibitor, was synthesized in good yield via 9 steps from vanillin. The asymmetric synthesis was achieved effectively by a modified Oae's asymmetric oxidation of diaryl sulfide. A mechanism involving pentacoordinated sulfurane intermediates was supported by the molecular modeling.

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Asymmetric Synthesis of a Xanthine Dehydrogenase Inhibitor (S)-(–)-BOF-4272 : Mechanism of Chiral Diaryl Sulfoxide Formation

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Asymmetric Synthesis of a Xanthine Dehydrogenase Inhibitor (S)-(–)-BOF-4272 : Mechanism of Chiral Diaryl Sulfoxide Formation

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