Synthesis of novel chiral [2.2.1]cryptands incorporating sugars

Chiral N, N'-dimethyl diaza-crown ethers bearing functionalized α-D-gluco-, α-D-galacto-, and α-D-mannopyranoside residues are transformed into the corresponding 2.2.1]cryptands with bis(2-iodoethyl) ether under high-pressure conditions and subsequent demethylation. Alternatively, α-D-manno-diaza-18-crown-6 reacts with diglycolic acid dichloride under high-dilution conditions to form bisamide which is reduced to the corresponding chiral 2.2.1]cryptand.