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【结 构 式】

【分子编号】46956

【品名】S-(tert-butyl) 3-oxooctadecanethioate

【CA登记号】

【 分 子 式 】C22H42O2S

【 分 子 量 】370.64028

【元素组成】C 71.29% H 11.42% O 8.63% S 8.65%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(V)

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.

1 Sodeoka, M.; et al.; Asymmetric synthesis of a 3-acyltetronic acid derivative, RK-682, and formation of its calcium salt during silica gel column chromatography. Chem Pharm Bull 2001, 49, 2, 206.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 20917 methyl (4R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 52373-72-5 C7H12O4 详情 详情
(II) 20916 methyl (2R)-2,3-dihydroxypropanoate C4H8O4 详情 详情
(III) 46955 methyl (2R)-2-hydroxy-3-(trityloxy)propanoate C23H22O4 详情 详情
(IV) 27918 palmitic acid 57-10-3 C16H32O2 详情 详情
(V) 46956 S-(tert-butyl) 3-oxooctadecanethioate C22H42O2S 详情 详情
(VI) 46957 (1R)-2-methoxy-2-oxo-1-[(trityloxy)methyl]ethyl 3-oxooctadecanoate C41H54O6 详情 详情
(VII) 46958 (5R)-3-palmitoyl-5-[(trityloxy)methyl]-2,4(3H,5H)-furandione C40H50O5 详情 详情
Extended Information