Regioselective Conversion of Primary Alcohols into Iodides in Unprotected Methyl Furanosides and Pyranosides
Philip R. Skaanderup, Carina Storm Poulsen, Lene Hyldtoft, Malene R. Jørgensen, Robert Madsen*
*Department of Chemistry, Building 201, Technical University of Denmark, 2800 Lyngby, Denmark, Email: rmkemi.dtu.dk
P. R. Skaanderup, C. S. Poulsen, L. Hyldtoft, M. R. Jørgensen, R. Madsen, Synthesis, 2002, 1721-1727.
Two methods are described for the regioselective displacement of the primary hydroxy group in methyl glycosides with iodide. Products of the first method employing triphenylphosphine and iodine need purification on a reverse phase column. A one-pot procedure via sulfonates and subsequent substitution with iodide and methods for the protection of the iodoglycosides are also described.
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