RK-682

Chemical Name: 3-Hexadecanoyl-5-(hydroxymethyl)tetrahydrofuran-2,4-dione
项目整合开发状态: Preclinical
项目研究机构:
合成路线:An efficient synthesis of the optically active compound has been reported.Acid hydrolysis of the chiral acetonide (I) gave dihydroxy ester (II),which was selectively protected at the primary hydroxyl group as the O-trityl derivative (III).The beta-keto thioester (V) was obtained by condensation of palmitic acid (IV) with the magnesium salt of [(tert-butylthio)carbonyl]acetic acid via activation with carbonyl diimidazole.Silver salt-promoted condensation of thioester (V) with hydroxy ester (III) gave adduct (VI).The 3-acyltetronic acid system (VII) was obtained by cyclization of (VI) in the presence of tetrabutylammonium fluoride.Finally,deprotection of the trityl group using 1 N HCl afforded the title compound.