Regioselective synthesis and characterization of naphthylethylcarbamoyl-beta-cyclodextrins.
Regioselective reactions of 1-(1-naphthyl)ethyl isocyanate (NEIC) with beta-cyclodextrin (beta-CD) were studied with and without NaH activation of beta-CD in N,N-dimethylformamide (DMF) and pyridine. All six possible monosubstituted CD products were separated and characterized by proton NMR. Primary substitution product predominates when the reaction was carried out under reflux condition in pyridine without NaH activation. The C-2 substitution product predominates when the reaction was carried out in DMF. Conversion of 2-O-(1-(1-naphthyl)ethylcarbamoyl)-beta-CD to 6-O-(1-(1-naphthyl)ethylcarbamoyl)-beta-CD was observed when NaH was used to activate hydroxyl groups of CD.
Gahm
K H
KH
Department of Chemistry, University of Hawaii at Manoa, Honolulu 96822.
Yoshida
W
W
Niemczura
W P
WP
Stalcup
A M
AM
D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003505:Cyclodextrins; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D016339:Spectrometry, Mass, Fast Atom Bombardment; D047392:beta-Cyclodextrins
D002219:Carbamates; D003505:Cyclodextrins; D007202:Indicators and Reagents; D047392:beta-Cyclodextrins; C031215:betadex