Facile preparation of mono-2-O-modified eicosa-O-methylcyclomaltoheptaoses (-beta-cyclodextrins).
Mono-2-O-benzylated eicosa-O-methylcyclomaltoheptaose (-beta-cyclodextrin) was prepared in one pot from cyclomaltoheptaose (beta-cyclodextrin) in 33% isolated yield and quantitatively converted to mono-2-OH-free eicosa-O-methylcyclomaltoheptaose, which is the key compound for further modification. Transformation of this 2-OH group successfully gave several mono-2-O-modified eicosa-O-methylcyclomaltoheptaoses such as the acetate, the N,N-dimethylcarbamate, the N-n-butylcarbamate, the methanesulfonate, and the S-methyldithiocarbonate.
Suzuki
Masato
M
Department of Organic and Polymeric Materials, Graduate School of Science and Engineering, and International Research Center of Macromolecular Science, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Japan. msuzuki@polymer.titech.ac.jp
Nozoe
Yutaka
Y
D000085:Acetates; D000476:Alkanesulfonates; D002219:Carbamates; D002264:Carboxylic Acids; D003505:Cyclodextrins / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D047392:beta-Cyclodextrins
D000085:Acetates; D000476:Alkanesulfonates; D002219:Carbamates; D002264:Carboxylic Acids; D003505:Cyclodextrins; D047392:beta-Cyclodextrins; C031215:betadex