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Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
362
Identifiers
DOI: 10.1016/j.carres.2012.08.021
Keywords
  • Per-Tert-Butyldimethylsilyl-β-D-Galactofuranose
  • Galactofuranosyl Iodide
  • C-Galactofuranosylation
  • S-Galactofuranosylation
Disciplines
  • Biology

Abstract

Abstract The use of the easily available persilylated derivative 1 for the synthesis of C- and S-Galf derivatives has been investigated. By anomeric iodination of 1 with TMSI, followed by in situ coupling with C- and S-nucleophiles under very mild conditions and in the absence of promoters, derivatives with value as glycomimetics or as precursors of glycobiological tools were synthesized. Among them, the synthesis of the isolable 1-galactofuranosylthiol 15 is remarkable, as it paves the way for alternative approaches for S-galactofuranosyl derivatives.

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