A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, ß-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges.
Beilstein J Org Chem
; 10: 1390-6, 2014.
Article
in En
| MEDLINE
| ID: mdl-24991293
ABSTRACT
An efficient synthetic route toward the preparation of a complete series of monosubstituted tetraalkylammonium cyclodextrin (CD) derivatives is presented. Monotosylation of native CDs (α-, ß-, γ-) at position 6 gave the starting material. Reaction of monotosylate (mono-Ts-CD) with 45% aqueous trimethylamine gave CDs substituted with one cationic functional group in a single step. Derivatives equipped with a substituent containing two cationic sites separated by an ethylene or a propylene linker were prepared by reacting mono-Ts-CD with neat N,N,N'-trimethylethane-1,2-diamine or N,N,N'-trimethylpropane-1,3-diamine and subsequent methylation by CH3I in good yields. Finally, analogues bearing a moiety with three tetraalkylammonium sites were synthesized by reacting mono-Ts-CD with bis(3-aminopropyl)amine and subsequent methylation. The majority of the presented reactions are very straightforward with a simple work-up, which avoids the need of chromatographic separation. Thus, these reactions are suitable for the multigram-scale production of monosubstituted cationic CDs.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Beilstein J Org Chem
Year:
2014
Document type:
Article
Affiliation country:
Czech Republic