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【结 构 式】 
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【药物名称】CGP-31608 【化学名称】(5R,6S,1'R)-2-(Aminomethyl)-6-(1'-hydroxyethyl)-penem-3-carboxylic acid 【CA登记号】107740-67-0 【 分 子 式 】C9H12N2O4S 【 分 子 量 】244.27099 |
【开发单位】Novartis (Originator) 【药理作用】Penems |
合成路线1
Substitution with sodium [N-(allyloxycarbonyl)amino]thioacetate of the tert-butylsulfonyl group of the (3S,4R)-azetidinone (I) (obtained in several steps from L threonine), with overall retention of configuration at C-4, gives the azetidinone (II), wnich is converted with allyloxalyl chloride to the oxamide (III). Cyclization of (III) with triethylphosphite yields the (5R,6S,1'R)-allyl-2-(allyloxycarbonylaminomethyl)-6-(1'-allyloxycarbonyloxyethyl)penem-3-carboxylate (IV), which is deprotected to yield crystalline CGP-31608.
| 【1】 Gregg, C.; Tioutiounnik, N.; Dempsey, W.; Revankar, S.; Helv Chim Acta 1986, 69, 1576. |
| 【2】 Cozens, R.M.; Lang, M.; CGP-31608. Drugs Fut 1988, 13, 1, 19. |
| 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) | 21563 | allyl (1R)-1-[(2R,3S)-2-(tert-butylsulfonyl)-4-oxoazetidinyl]ethyl carbonate | C13H21NO6S | 详情 | 详情 | |
| (II) | 21564 | S-[(2R,3S)-3-((1R)-1-[[(allyloxy)carbonyl]oxy]ethyl)-4-oxoazetidinyl] 2-[[(allyloxy)carbonyl]amino]ethanethioate | C15H20N2O7S | 详情 | 详情 | |
| (III) | 21565 | allyl 2-[(2R,3S)-2-[(2-[[(allyloxy)carbonyl]amino]acetyl)sulfanyl]-3-((1R)-1-[[(allyloxy)carbonyl]oxy]ethyl)-4-oxoazetidinyl]-2-oxoacetate | C20H24N2O10S | 详情 | 详情 | |
| (IV) | 21566 | allyl (5R,6S)-3-([[(allyloxy)carbonyl]amino]methyl)-6-((1R)-1-[[(allyloxy)carbonyl]oxy]ethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C20H24N2O8S | 详情 | 详情 | |
| (V) | 21567 | sodium 2-[[(allyloxy)carbonyl]amino]ethanethioate | C6H8NNaO3S | 详情 | 详情 | |
| (VI) | 15585 | allyl 2-chloro-2-oxoacetate | C5H5ClO3 | 详情 | 详情 |
Extended Information