Migration of secondary tert-butyldimethylsilyl groups in cyclomalto-heptaose and -octaose derivatives

Add time:08/28/2019    Source:sciencedirect.com

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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