84346-53-2Relevant academic research and scientific papers
Migration of secondary tert-butyldimethylsilyl groups in cyclomalto-heptaose and -octaose derivatives
Icheln, Detlef,Gehrcke, Baerbel,Piprek, Yvonne,Mischnick, Petra,Koenig, Wilfried A.,Dessoy, Marco A.,Morel, Ademir F.
, p. 237 - 250 (1996)
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.
Effective syntheses of per-2,3-di- and per-3-O-chloroacetyl-β-cyclodextrins: A new kind of ATRP initiators for star polymers
Guo, Zhizhang,Chen, Xingyu,Zhang, Xiao,Xin, Jianyu,Li, Jianshu,Xiao, Huining
scheme or table, p. 2351 - 2353 (2010/06/13)
Selective chloroacetylations at per-2,3- and per-3-positions of β-cyclodextrin have been achieved via protection-deprotection methods. The reaction condition of pH >4 controlled by appropriate proton scavenger is essential for obtaining designed chloroacetylation degree under effective protection, as well as for high yield with less side-products. The β-cyclodextrin derivatives with 14 or 7 chloroacetyl groups are useful initiators for synthesizing star polymers with well-defined structure by atom transfer radical polymerization.
Binding and catalytic properties of 2-0-and 3-o-permethylated cyclodextrins
Nagata, Takuya,Yoshikiyo, Keisuke,Matsui, Yoshihisa,Yamamoto, Tatsuyuki
experimental part, p. 196 - 201 (2009/05/30)
Hexakis(3-0-methyl)-α,-cyclodextrin (3α) bound tom-and p-nitrophenolate ions more strongly, whereas hexakis(2-0-methy1)-α- cyclodextrin (2α) bound less strongly than native α-cyclodextrin. ROESY spectra showed that the 3-0-mefhyl groups of 3a interact with the guest protons, whereas 2-0-methyl groups of 2a do not. 3a accelerated and 2a decelerated the cleavage of m-nitrophenyl acetate in an alkaline solution, suggesting that the C(2)-OH of α-cyclodextrin is more catalytic than the C(3)-OH. However, the catalytic effect of 3a was much smaller than that of native a-cyclodextrin. Loss of hydrogen bonding between the C(3)-OH and C(2)-OH by 3-O-permethylation is responsible for the small catalytic effects of 3α. Similar results were obtained for β-cyclodextrin analogs.
