A new mixed acetal-type substitution pattern for alpha-cyclodextrin. Preparation of hexakis (3-O-benzyl)- alpha-cyclodextrin

A Lipták; L Jánossy; G Batta; A Borbás; J Szejtli

A new mixed acetal-type substitution pattern for alpha-cyclodextrin. Preparation of hexakis (3-O-benzyl)- alpha-cyclodextrin

Carbohydr Lett. 2001;4(2):111-6.

Authors

A Lipták¹, L Jánossy, G Batta, A Borbás, J Szejtli

Affiliation

¹ Research Group for Carbohydrates of the Hungarian Academy of Sciences, Institute of Biochemistry, L. Kossuth University, Debrecen. liptaka@tigris.klte.hu

PMID: 11506155

Abstract

alpha-CD was converted into hexakis[2,6-di-O-(methoxydimethyl)methyl]-alpha-CD by a proton-catalyzed reaction with 2-methoxypropene. Subsequent benzylation under Brimacombe conditions resulted in the fully protected compound, from which the acid-sensitive acetal groups were removed to obtain hexakis(3-O-benzyl)-alpha-cyclodextrin. The structure of all of the compounds synthesized was confirmed by 13C J-ECHO, COSY, HETCOR and HMBC NMR measurements.