MIGRATION OF SECONDARY TERT-BUTYLDIMETHYLSILYL GROUPS IN CYCLOMALTO-HEPTAOSE AND CYCLOMALTO-OCTAOSE DERIVATIVES

Authors
ICHELN D GEHRCKE B PIPREK Y MISCHNICK P KONIG WA DESSOY MA MOREL AF
Citation
D. Icheln et al., MIGRATION OF SECONDARY TERT-BUTYLDIMETHYLSILYL GROUPS IN CYCLOMALTO-HEPTAOSE AND CYCLOMALTO-OCTAOSE DERIVATIVES, Carbohydrate research, 280(2), 1996, pp. 237-250
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Carbohydrate research → ACNP
ISSN journal
00086215
Volume
280
Issue
2
Year of publication
1996
Pages
237 - 250
Database
ISI
SICI code
0008-6215(1996)280:2<237:MOSTGI>2.0.ZU;2-V
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-buty ldimethylsilyl. groups occurs, leading to n)yl-3,6-di-O-tert-butyidime thylsilyl-cyclodextrin derivatives. The detection and identification o f the reaction step during which migration occurred is described and p ossible mechanisms of migration are discussed.