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【结 构 式】

【分子编号】31278

【品名】ethyl (1S,9S,10S,13R,14R,17R)-3-[(ethoxycarbonyl)oxy]-17-[(1R)-2-(4-hydroxy-4-methyl-5-oxotetrahydro-2-furanyl)-1-methylethyl]-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-1-carboxylate

【CA登记号】

【 分 子 式 】C33H48O8

【 分 子 量 】572.73932

【元素组成】C 69.2% H 8.45% O 22.35%

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)

The less polar major isomer (IVa) was reduced to lactone (IVb) with 10 eq of tri-n-butyltin hydride (tetrahydrofuran, room temperature, 4 h) in 88% yield. Treatment of the lactone (IVb) with a catalytic amount of HCl in methanol at 50 C for 5 h gave the diol (IVc) in 88% yield. Reaction of (IVc) with ethyl chloroformate (16 eq) in the presence of 4-dimethylaminopyridine (17 eq) at room temperature for 15 h afforded ethyl carbonate (IVd) in 82% yield. Allylic bromination of (IVd) with 0.6 eq of 1,3-dibromo-5,5-dimethylhydantoin in n-hexane under reflux followed by dehydrobromination with collidine in refluxing xylene gave the 5,7-diene (V) as the major product. Alkaline hydrolysis (KOH, methanol, room temperature, 15 h) and purification by preparative thin-layer chromatography (TLC) gave the 5,7-diene in 53% yield from (IVd).

1 Morris, D.S.; Norris, A.F.; Williams, D.H.; Structure and synthesis of 25-hydroxycholecalciferol-26,23-lactone, a metabolite of vitamin D3. J Org Chem 1981, 46, 3422-28.
2 Seino, Y.; Ishizuka, S.; 23(S),25(R)-1alpha,25-(OH)2-D3-26,23-Lactone. Drugs Fut 1992, 17, 8, 655.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IVa) 31272 5-[(2S)-2-[(1S,8S,9S,10R,13S,14S,17R)-1,3-bis(methoxymethoxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-iodopropyl]-3-hydroxy-3-methyldihydro-2(3H)-furanone C31H49IO7 详情 详情
(IVb) 31273 5-[(2R)-2-[(1S,8S,9S,10R,13R,14S,17R)-1,3-bis(methoxymethoxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]-3-hydroxy-3-methyldihydro-2(3H)-furanone C31H50O7 详情 详情
(IVc) 31274 5-[(2R)-2-[(1S,8S,9S,10R,13R,14S,17R)-1,3-dihydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]-3-hydroxy-3-methyldihydro-2(3H)-furanone C27H42O5 详情 详情
(F) 31275 N,N-dimethyl-N-(4-pyridinyl)amine; N,N-dimethyl-4-pyridinamine 1122-58-3 C7H10N2 详情 详情
(IVd) 31276 (1S,8S,9S,10R,13R,14S,17R)-1-[(ethoxycarbonyl)oxy]-17-[(1R)-2-(4-hydroxy-4-methyl-5-oxotetrahydro-2-furanyl)-1-methylethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ethyl carbonate C33H50O9 详情 详情
(G) 31277 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione 77-48-5 C5H6Br2N2O2 详情 详情
(V) 31278 ethyl (1S,9S,10S,13R,14R,17R)-3-[(ethoxycarbonyl)oxy]-17-[(1R)-2-(4-hydroxy-4-methyl-5-oxotetrahydro-2-furanyl)-1-methylethyl]-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-1-carboxylate C33H48O8 详情 详情
Extended Information