Simple preparation of 3I-O-substituted beta-cyclodextrin derivatives using cinnamyl bromide.
[reaction: see text] A new method for preparation of 3(I)-O-substituted beta-cyclodextrin derivatives was developed. Cinnamyl bromide reacts with beta-cyclodextrin to form predominantly the 3(I)-O-cinnamyl derivative (30% isolated yield, >90% regioselectivity). After protection of the remaining cyclodextrin hydroxyls by acetylation, the cinnamyl group can be easily transformed to many other groups (exemplified by transformation to 3(I)-O-carboxymethyl derivative). Substitution pattern in singly modified CDs was unambiguously determined by a combination of 2D NMR techniques.
Jindrich
Jindrich
J
Department of Organic Chemistry, Charles University, Faculty of Science, Prague, Czech Republic. jindrich@natur.cuni.cz
Tislerová
Iva
I