(3S,4R)-4-[(1R)-3-bromo-1-methyl-2-oxopropyl]-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-2-azetidinone -Drug Synthesis Database

【结构式】

【分子编号】30146

【品名】(3S,4R)-4-[(1R)-3-bromo-1-methyl-2-oxopropyl]-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-2-azetidinone

【CA登记号】

【分子式】C₁₅H₂₈BrNO₃Si

【分子量】378.38176

【元素组成】C 47.61% H 7.46% Br 21.12% N 3.7% O 12.69% Si 7.42%

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：(XXXIV)

Azetidinepropanoic acid (XXXI) was converted to methoxyamide (XXXII) and then treated with trimethylsilylmethyllithium to give silyl ketone (XXXIII). After conversion of (XXXIII) to bromoketone (XXXIV), displacement by an acetate group afforded acetoxymethyl ketone (XXXV). A similar route as above produced phosphorane (XXXVI), which was then cyclized to the carbapenem (XXXVII).

参考文献中间体

合成目标

【1】 Yasuda, N.; et al.; Preparation of anti-MRS carbapenem L-786,392. 38th Intersci Conf Antimicrob Agents Chemother (Sept 24 1998, San Diego) 1998, Abst F-31.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXXI)	30029	(2R)-2-[(2S,3S)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetidinyl]propionic acid	C₁₄H₂₇NO₄Si	详情	详情
(XXXII)	30030	(2R)-2-[(2S,3S)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetidinyl]-N-methoxy-N-methylpropanamide	C₁₆H₃₂N₂O₄Si	详情	详情
(XXXIII)	30145	(3S,4R)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-[(1R)-1-methyl-2-oxo-3-(trimethylsilyl)propyl]-2-azetidinone	C₁₈H₃₇NO₃Si₂	详情	详情
(XXXIV)	30146	(3S,4R)-4-[(1R)-3-bromo-1-methyl-2-oxopropyl]-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-2-azetidinone	C₁₅H₂₈BrNO₃Si	详情	详情
(XXXV)	30147	(3R)-3-[(2R,3S)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetidinyl]-2-oxobutyl acetate	C₁₇H₃₁NO₅Si	详情	详情
(XXXVI)	30148	(3R)-3-[(2R,3S)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-1-[3-(4-nitrobenzyloxy)-2-oxo-1-(triphenylphosphoranylidene)propyl]-4-oxoazetidinyl]-2-oxobutyl acetate	C₄₄H₅₁N₂O₉PSi	详情	详情
(XXXVII)	30149	4-nitrobenzyl (4S,5R,6S)-6-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-3-(hydroxymethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	C₂₄H₃₄N₂O₇Si	详情	详情

Extended Information