Isoxazolidin-5-one analogs of β-lactam antibiotics

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• 作者：Panfil ; Irma ; Urbanczyk-Lipkowska ; Zofia ; Chmielewski ; Marek
• 关键词：Isoxazolidin-5-ones ; Analogs of β ; -lactams ; 2 ; 4 ; 5-Trisubstituted 1-aza-3 ; 9-dioxa-8-oxo-bicyclo[4.3.0]nonanes
• 刊名：Carbohydrate Research
• 出版年：1998
• 出版时间：January, 1998
• 年：1998
• 卷：306
• 期：4
• 页码：505-515
• 全文大小：302 K

文摘

Isoxazolidin-5-ones, readily available via conjugate addition–rearrangement of hydroxylamine to α,β-unsaturated sugar 1,5-lactones, react with aldehydes and diethoxymethyl acetate to afford 2,4,5-trisubstituted 1-aza-3,9-dioxa-8-oxo-bicyclo[4.3.0]nonanes. 4,5-Disubstituted 1-aza-2-butoxycarbonyl-3,9-dioxa-8-oxo-bicyclo[4.3.0]nonanes undergo base-catalyzed rearrangement to 4,6-disubstituted butyl 2,3-dideoxy-3-N-oxamate-d-ribohexaldono-1,5-lactones. The configuration of representative compounds: (2S,4R,5S,6S) 5-acetoxy-4-acetoxymethyl-1-aza-3,9-dioxo-2-methyl-8-oxo-bicyclo[4.3.0]nonane and butyl 4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-3-N-oxamate-d-ribohexaldono-1,5-lactone were proved by X-ray crystallography.