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【结 构 式】 
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【分子编号】39552 【品名】benzyl 3-[((2R,3R)-1-[2-(benzhydryloxy)-1-chloro-2-oxoethyl]-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)amino]-2-[4-(benzyloxy)phenyl]-3-oxopropanoate 【CA登记号】 |
【 分 子 式 】C47H43ClN6O10S 【 分 子 量 】919.41156 【元素组成】C 61.4% H 4.71% Cl 3.86% N 9.14% O 17.4% S 3.49% |
合成路线1
该中间体在本合成路线中的序号：(XIII)The isopropylidene group of (X) is oxidized with ozone affording the corresponding diketonic compound (XI), which is reduced selectively with Zn and acetic acid yielding the hydroxy ketone (XII). The reaction of (XII) with SOCl2 affords the corresponding chloro ketone (XIII), which is treated with triphenylphosphine in a basic medium to give alpha-[3beta-[alpha-(p-benzyloxyphenyl)-alpha-(benzyloxycarbonyl)acetamido]-3alpha-methoxy-4beta-[-3-(1-methyltetrazol-5-yl)thiomethyl-2-oxopropoxy]-2-oxoazetidine-1-yl]-alpha-triphenylphosphoranylideneacetic acid diphenylmethyl ester (XIV). Finally, this compound is treated with refluxing dioxane affording the protected 1-oxa-dethia-3-cephem compound (XV), which is deprotected with trifluoroacetic acid in anisole.
| 【1】 Serradell, M.N.; Blancafort, P.; Castaner, J.; S-6059. Drugs Fut 1979, 4, 9, 667. |
| 【2】 Narisada, M.; Nagata, W. (Shionogi & Co. Ltd.); Arylmalonamido-1-oxadethiacephalosporins. DE 2713370; US 4138486 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 39549 | benzhydryl 2-((2R,3R)-3-([3-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-oxopropanoyl]amino)-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)-3-methyl-2-butenoate | C50H48N6O10S | 详情 | 详情 | |
| (XI) | 39550 | benzyl 3-[((2R,3R)-1-[2-(benzhydryloxy)-2-oxoacetyl]-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)amino]-2-[4-(benzyloxy)phenyl]-3-oxopropanoate | C47H42N6O11S | 详情 | 详情 | |
| (XII) | 39551 | benzyl 3-[((2R,3R)-1-[2-(benzhydryloxy)-1-hydroxy-2-oxoethyl]-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)amino]-2-[4-(benzyloxy)phenyl]-3-oxopropanoate | C47H44N6O11S | 详情 | 详情 | |
| (XIII) | 39552 | benzyl 3-[((2R,3R)-1-[2-(benzhydryloxy)-1-chloro-2-oxoethyl]-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)amino]-2-[4-(benzyloxy)phenyl]-3-oxopropanoate | C47H43ClN6O10S | 详情 | 详情 | |
| (XIV) | 39553 | benzyl 3-[((2R,3R)-1-[2-(benzhydryloxy)-2-oxo-1-(triphenylphosphoranylidene)ethyl]-3-methoxy-2-[3-[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]-2-oxopropoxy]-4-oxoazetidinyl)amino]-2-[4-(benzyloxy)phenyl]-3-oxopropanoate | C65H57N6O10PS | 详情 | 详情 | |
| (XV) | 38604 | benzhydryl (6R,7R)-7-([3-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-oxopropanoyl]amino)-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C47H42N6O9S | 详情 | 详情 |