Synthesis of carbamate-containing cyclodextrin analogues

The one pot cyclooligomerization of a saccharide-derived p-nitrophenyl carb amate monomer was developed to generate a series of novel carbamate contain ing cyclodextrin analogues. The "transcarbamoylation" occurs by initial bas e induced activation to the isocyanate, followed by polycondensation/cycliz ation of the isocyanato alcohol. In the presence of NaH, only cyclized olig omers were observed, suggesting the importance of Na+ in promoting the effi ciency of the cyclization process. The facile deprotection of the oligomers was achieved.