ArticleRSC advances2024
Syntheses of optically active monapterin, 7,8-dihydromonapterin, and 5,6,7,8-tetrahydromonapterin from l-xylose.
Article in RSC advances, 2024. 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
We describe the syntheses of monapterin, dihydromonapterin and tetrahydromonapterin in optically active forms. The syntheses involved the condensation of l-xylose with phenylhydrazine, providing a hydrazone derivative. The reaction of the resulting hydrazone with triamino-pyrimidinone followed by oxidation of the resulting pteridinone with molecular oxygen furnished pterin containing a hydroxylated side chain. Hydrogenation of the pterin derivatives over RANEY® Ni catalyst afforded dihydromonapterin and tetrahydromonapterin in optically active forms. We also investigated an alternative route involving an Amadori rearrangement, followed by the Polonovski-Boon reaction as the key step to make these monapterin derivatives.
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