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Isoxazolidin-5-one analogs ofβ-lactam antibiotics

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
306
Issue
4
Identifiers
DOI: 10.1016/s0008-6215(97)10107-0
Keywords
  • Isoxazolidin-5-Ones
  • Analogs Ofβ-Lactams
  • 2
  • 4
  • 5-Trisubstituted 1-Aza-3
  • 9-Dioxa-8-Oxo-Bicyclo[4.3.0]Nonanes

Abstract

Abstract 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: (2 S,4 R,5 S,6 S) 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.

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