Tetrahedron: Asymmetry

Fluoridolysis of 5, 6-epoxy carbohydrates: application to the synthesis of 5-fluoro lactosamine and isolactosamine glycosides

TL Hagena, JK Coward

Index: Hagena, Tara L.; Coward, James K. Tetrahedron Asymmetry, 2009 , vol. 20, # 6-8 p. 781 - 794

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Citation Number: 3

Abstract

The synthesis of 6-selenophenyl derivatives of β-1, 3 and β-1, 4 disaccharides has been explored for the purpose of extending our epoxide fluoridolysis methodology to the synthesis of 5-fluoro analogues of N-acetyl isolactosamine (isoLacNAc, lacto-N-biose) and N-acetyl lactosamine (LacNAc) glycosides. Successful synthesis of the C-6 selenium-containing disaccharides was achieved via Lewis acid-mediated donor and acceptor substrates, the ...