Migration of secondary tert-butyldimethylsilyl groups in cyclomalto-heptaose and -octaose derivatives.
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.
Icheln
D
D
Institut für Organische Chemie, Universität Hamburg, Germany.
Gehrcke
B
B
Piprek
Y
Y
Mischnick
P
P
König
W A
WA
Dessoy
M A
MA
Morel
A F
AF
D000107:Acetylation; D002240:Carbohydrate Sequence; D003505:Cyclodextrins / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008757:Methylglucosides / Q000737:chemistry*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D047392:beta-Cyclodextrins; D047408:gamma-Cyclodextrins
D003505:Cyclodextrins; D008757:Methylglucosides; D017646:Organosilicon Compounds; D047392:beta-Cyclodextrins; D047408:gamma-Cyclodextrins; C009660:t-butyldimethylsilyl compounds; C027020:methylglucoside; C031215:betadex; C023792:gamma-cyclodextrin