| Abstract | A new method for preparation of 3I-O-substituted beta-cyclodextrin derivatives was developed. Cinnamyl bromide reacts with beta-cyclodextrin to form predominantly the 3I-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 3I-O-carboxymethyl derivative). Substitution pattern in singly modified CDs was unambiguously determined by a combination of 2D NMR techniques. |
