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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:

P. R. Skaanderup, C. S. Poulsen, L. Hyldtoft, M. R. Jørgensen, R. Madsen, Synthesis, 2002, 1721-1727.

DOI: 10.1055/s-2002-33641


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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Key Words

carbohydrates, halogenation, iodination, regioselectivity, substitution, sulfonates, silyl ethers, benzyl ethers

ID: J66-Y2002-1630