Abstract
When 2,6-di- O- tert-butyldimethylsilylated cyclomalto-oligosaccharides (cyclodextrins) are treated with allyl or methyl iodide and NaH in dry tetrahydrofuran, O-2 → O-3 migration of the secondary 2- O- tert-butyldimethylsilyl groups occurs, leading to 2- O-alk(en)yl-3,6-di- O- tert-butyldimethylsilyl-cyclodextrin derivatives. The detection and identification of the reaction step during which migration occurred is described and possible mechanisms of migration are discussed.
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