Synthesis of carbamate-containing cyclodextrin analogues.
[formula: see text] The one-pot cyclooligomerization of a saccharide-derived p-nitrophenyl carbamate monomer was developed to generate a series of novel carbamate-containing cyclodextrin analogues. The "transcarbamoylation" occurs by initial base-induced activation to the isocyanate, followed by polycondensation/cyclization of the isocyanato alcohol. In the presence of NaH, only cyclized oligomers were observed, suggesting the importance of Na+ in promoting the efficiency of the cyclization process. The facile deprotection of the oligomers was achieved.
Chong
P Y
PY
Department of Chemistry, University of Illinois at Urbana-Champaign 61801, USA.
Petillo
P A
PA
D002219:Carbamates / Q000737:chemistry*; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D002219:Carbamates; D003505:Cyclodextrins