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【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