【药物名称】RK-682
化学结构式(Chemical Structure):
参考文献No.607799
标题:Asymmetric synthesis of a 3-acyltetronic acid derivative, RK-682, and formation of its calcium salt during silica gel column chromatography
作者:Sodeoka, M.; Sampe, R.; Kojima, S.; Baba, Y.; Morisaki, N.; Hashimoto, Y.
来源:Chem Pharm Bull 2001,49(2),206
合成路线图解说明:

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.

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