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【结 构 式】 
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【分子编号】54856 【品名】(3S,4R)-3-((1S)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-(methylsulfanyl)-2-azetidinone 【CA登记号】 |
【 分 子 式 】C12H25NO2SSi 【 分 子 量 】275.48754 【元素组成】C 52.32% H 9.15% N 5.08% O 11.62% S 11.64% Si 10.19% |
合成路线1
该中间体在本合成路线中的序号：(XIV)In an alternative route, intermediate (VI) was prepared from the previously reported azetidinone (XIII), possessing the adequate alcohol group configuration. Displacement of the acetoxy group of (XIII) with sodium methanethiolate gave sulfide (XIV). The azetidinone N was then alkylated with p-nitrobenzyl iodoacetate (XV) to afford azetidineacetate (XVI). Acylation of the lithium enolate of ester (XVI) by pivaloyl chloride (II) provided keto ester (XVII). Intermediate (VI) was then obtained by desilylation of (XVII) with tetrabutylammonium fluoride.
| 【1】 Pfaendler, H.R. (Eli Lilly and Company); (1'S)-Hydroxyalkyloxapenem-3-carboxylic acids and their use as beta-lactamase inhibitors. DE 4142423; EP 0548790 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II) | 13597 | 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride | 3282-30-2 | C5H9ClO | 详情 | 详情 |
| (VI) | 54849 | 4-nitrobenzyl 2-[(2R,3S)-3-[(1S)-1-hydroxyethyl]-2-(methylsulfanyl)-4-oxoazetidinyl]-4,4-dimethyl-3-oxopentanoate | C20H26N2O7S | 详情 | 详情 | |
| (XIII) | 54855 | (2R,3R)-3-((1S)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-oxoazetidinyl acetate | C13H25NO4Si | 详情 | 详情 | |
| (XIV) | 54856 | (3S,4R)-3-((1S)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-(methylsulfanyl)-2-azetidinone | C12H25NO2SSi | 详情 | 详情 | |
| (XV) | 54841 | 4-nitrobenzyl 2-iodoacetate | C9H8INO4 | 详情 | 详情 | |
| (XVI) | 54857 | 4-nitrobenzyl 2-[(2R,3S)-3-((1S)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(methylsulfanyl)-4-oxoazetidinyl]acetate | C21H32N2O6SSi | 详情 | 详情 | |
| (XVII) | 54858 | 4-nitrobenzyl 2-[(2R,3S)-3-((1S)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(methylsulfanyl)-4-oxoazetidinyl]-4,4-dimethyl-3-oxopentanoate | C26H40N2O7SSi | 详情 | 详情 |