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Regioselective sulfonation of a secondary hydroxyl group of cyclodextrins

โœ Scribed by Teiichi Murakami; Kazuaki Harata; Satoshi Morimoto

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
248 KB
Volume
28
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A new and convenient procedure has been developed for the regioselective tosylation of a C-2 hydroxyl group of cyclodextrins via cyclic tin intermediate. Cyclodextrin(CD)s (1) have attracted current interests as enzyme mimics' and chemical modification of CDs with various functional groups has been extensively investigated in order to produce more effective models. 2 Generally, the first important step to attach functional group to CD is sulfonation of hydroxyl groups.

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Selective sulfonation of a secondary hyd
Selective sulfonation of a secondary hydroxyl group of ฮฒ-cyclodextrin
โœ Akihiko Ueno; Ronald Breslow ๐Ÿ“‚ Article ๐Ÿ“… 1982 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 213 KB

Tosylation of the secondary side of S-cyclodextrin, which has previously been incorrectly reported, can be achieved by tosyl transfer from 3-nitrophenyl toluenesulfonate to the C-2 hydroxyl of the cyclodextrin. Cyclodextrins are toroidal cyclic oligosaccharides with the secondary hydroxyls of gluco

Regioselective silylation of C-2 hydroxy
Regioselective silylation of C-2 hydroxyl group of ฮฑ-cyclodextrin dependent on reaction temperature
โœ Katsunori Teranishi; Fumiko Ueno ๐Ÿ“‚ Article ๐Ÿ“… 2002 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 96 KB

Silylations of the C-2 hydroxyl group of a-cyclodextrin were carried out using t-butyldimethylsilyl imidazole in the presence of 4 A , molecular sieves in N,N-dimethylformamide. A unique aspect of this silylation method is the temperature dependence of the regioselectivity; silylation at 0ยฐC regiose