Regioselective conversion of primary alcohols into iodides in unprotected methyl furanosides and pyranosides

@article{Skaanderup2002RegioselectiveCO,
  title={Regioselective conversion of primary alcohols into iodides in unprotected methyl furanosides and pyranosides},
  author={P. Skaanderup and C. S. Poulsen and L. Hyldtoft and M. J{\o}rgensen and R. Madsen},
  journal={Synthesis},
  year={2002},
  volume={2002},
  pages={1721-1727}
}
Two methods are described for the regioselective displacement of the primary hydroxy group in methyl glycosides with iodide. The first method is a modification of a literature procedure employing triphenylphosphine and iodine, where purification has been carried out on a reverse phase column in order to efficiently separate the desired iodoglycosides from triphenylphosphine oxide. The second method employs a new procedure using sulfonylation in pyridine with sterically hindered 2,4,6-trichloro… Expand
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