The effective synthesis of a variety of bisthioureabridged calix [4]arenes substituted by carbohydrates units (D-glucose, D-mannose, D-galactose and lactose) at the narrow rim by reaction of bis(aminoethoxy)calix[4]arene 1 with glycosyl isothiocyanates is described.

The easy transformation of 5,11,17,23-tetra-tert-butyl-25,27bis(aminoethoxy)-26,28-dihydroxycalix[4]arene(2) into 5, 11,17,23-tetra-tert-butyl-26,28-dihydroxy-25,27-bis(2-isothiocyanoethoxy)calix[4]arene (3) and 5,11,17,23-tetra-tertbutyl-25,27-bis(chloroacetamidoethoxy)-26,28-dihydroxycalix[4]arene (4) has been exploited for the development of an efficient and expeditious synthesis of a variety of calix[4]3587 calix[4]arenes]. The functionality of compounds 2 and 3 allowed the formation of intramolecular bridges, leading to capped calix[4]arenes (compounds 5, 10, and 14) as well as to the construction of double calix[4]arene units by means of spacers containing thiourea or amide-sulfur groups (compounds 6 and 15, respectively). In addition, the bis(isothiocyanate) derivative 3 gave access to a high-yield preparation of heteroditopic bis(crown ether) calix[4]arenes (7−9) from commercial amino crown ethers.

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