Synthesis and characteriz.ation of highly water-sofuble di-functional β-cyclodextrin monomers

Department of Applied Chemistry, Faculty of Technology and Engineering, The M. S. University of Baroda,
P.O. Box 51, Kalabhavan, Vadodara-390 001, Gujarat, India

E-mail : chivukula_mn@yahoo.com

Manuscript received 5 December 2005, revised 25 August 2006, accept;d 25 August 2006

Highly water-soluble di-functional β-cyclodextrin monomers, including 6-diamino-6-deoxy β-cyclodextrin and 6-diisothiocyanate-6-deoxy β-cyclodextrin, have been synthesized. β-Cyclodextrin was first transformed into heptakis 6-deoxy-6-iodo and subsequently to heptakis 6-amino-6-deoxy derivative. Thus 6-diamino-6-deoxy β-cyclodextrin and 6-diisothiocyanate-6-deoxy β-cyclodextrin were prepared in an efficient route for the introduction of more reactive group on smaller rim of β-cyclodextrin without protection of primary and secondary hydroxyl groups. Cyclodextrin was endcapped with disulphonylchloride followed by neucleophilic substitution with sodium azide and subsequently reduced to an amine.These water-soluble monomers were characterized by FT-IR, ¹H NMR and mass spectroscopy.