Abstract
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- and 2,4,6-tribromobenzenesulfonyl chloride. The sulfonates thus formed are effective leaving groups and substitution with iodide can be carried out in a one-pot process. Protection of the iodoglycosides is also described either by benzylation with benzyl trichloroacetimidate or silylation with triethylsilyl chloride.
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