Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase.

@article{Manzano2012ConvenientSO,
  title={Convenient synthesis of 4-thiolactose, 3,4-dithiolactose and related thiooligosaccharides and disulfides. Inhibitory activity of the glycomimetics against a β-galactosidase.},
  author={Ver{\'o}nica E. Manzano and M. L. Uhrig and O. Varela},
  journal={Organic & biomolecular chemistry},
  year={2012},
  volume={10 44},
  pages={
          8884-94
        }
}
  • Verónica E. Manzano, M. L. Uhrig, O. Varela
  • Published 2012
  • Chemistry, Medicine
  • Organic & biomolecular chemistry
  • The ring-opening reaction of sugar 3,4-epoxides by 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranose (7) as a nucleophile led to (1 → 3)- and (1 → 4)-thiodisaccharides. High regio- and diastereoselectivities were achieved in the synthesis of the per-O-acetyl derivative of the β-D-Galp-S-(1 → 4)-4-thio-α-D-Glcp-O-iPr (10). Analogues of the 4-thiolactoside 10 have been prepared, with the β-D-Galp non-reducing end S-linked to D-Glcp, D-Gulp and D-Idop. A similar regioselective attack of 7 on C-4… CONTINUE READING
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