Synthesis of carbamate-containing cyclodextrin analogues

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.