DIRECT SYNTHESIS OF AMPHIPHILIC ALPHA-CYCLODEXTRINS, BETA-CYCLODEXTRINS, AND GAMMA-CYCLODEXTRINS

Authors
CHMURSKI K COLEMAN AW JURCZAK J
Citation
K. Chmurski et al., DIRECT SYNTHESIS OF AMPHIPHILIC ALPHA-CYCLODEXTRINS, BETA-CYCLODEXTRINS, AND GAMMA-CYCLODEXTRINS, Journal of carbohydrate chemistry, 15(7), 1996, pp. 787-796
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology
Journal title
Journal of carbohydrate chemistry → ACNP
ISSN journal
07328303
Volume
15
Issue
7
Year of publication
1996
Pages
787 - 796
Database
ISI
SICI code
0732-8303(1996)15:7<787:DSOAAB>2.0.ZU;2-#
Abstract
The clean one step synthesis of the amphiphilic alpha-, beta-, and gam ma-cyclodextrins starting from per-(6-bromo-6-deoxy)-alpha-, -beta-, a nd -gamma-cyclodextrins is described. The role of the lipophilic tail is played by various aryl groups (phenyl, p-bromophenyl, p-O-butoxyphe nyl, p-pentylphenyl, and o-, m-, and p-nitrophenyl) linked by a thioet her bridge to the position C-6 of each glucopyranose unit. The yields of the S-alkylation reactions were very high (85-95%).