Mixed acetals of cyclodextrins. Preparation of hexakis-, heptakis- and octakis[2,6-di-O-(methoxydimethyl)methyl]-alpha-, beta- and gamma-cyclodextrins.
The proton-catalyzed addition of 2-methoxypropene to alpha-, beta- and gamma-cyclodextrins resulted in hexakis-, heptakis-, and octakis[2,6-di-O-(methoxydimethyl)methyl]-alpha-, beta- and gamma-cyclodextrins, but no reaction was observed of CD-s with 2,2-dimethoxypropane. The mixed acetal-type compounds can be alkylated under basic conditions. The preparation of hexakis(3-O-benzyl)-alpha-cyclodextrin demonstrates the synthetic value of this methodology.
Lipták
András
A
Institute of Biochemistry, University of Debrecen, PO Box 55, H-4010 Debrecen, Hungary. liptaka@tigris.ktle.hu
Jánossy
Láránt
L
Borbás
Anikó
A
Szejtli
József
J
D000080:Acetals / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000478:Alkylation; D002384:Catalysis; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D011522:Protons
D000080:Acetals; D000475:Alkenes; D003505:Cyclodextrins; D011522:Protons; C013658:propylene