【结 构 式】 |
【分子编号】21567 【品名】sodium 2-[[(allyloxy)carbonyl]amino]ethanethioate 【CA登记号】 |
【 分 子 式 】C6H8NNaO3S 【 分 子 量 】197.190228 【元素组成】C 36.55% H 4.09% N 7.1% Na 11.66% O 24.34% S 16.26% |
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)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