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Isoxazolidin-5-one - isoxazolidine rearrangement, an entry to 3-amino-3-deoxy sugars

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
52
Issue
4
Identifiers
DOI: 10.1016/0040-4020(95)00967-1
Disciplines
  • Chemistry

Abstract

Abstract Conjugate addition - rearrangement of N-benzylhydroxylamine to α,β-unsaturated lactones 1 provides a short and effective route to 3-substituted isoxazolidin-5-ones. High and defined stereochemistry of this reaction with simultaneous liberation of the 5-OH group of the sugar chain, while all other groups remain protected, creates a possibility to switch from sugars of the D-configurational series to those of the L-series, thus providing a very attractive entry to important 3-amino-2,3-dideoxy sugars. Mesylation of the 2′-OH group of the isoxazolidin-5-one skeleton or introduction of an epoxide ring to C-2′,3′ carbon atoms and subsequent treatment of the molecule with a nucleophile causes isoxazolidin-5-one - isoxazolidine rearrangement with inversion of the configuration at the C-2 carbon atom.

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