Modification of D-glucose-based 18-crown-6 ethers by phosphorylation and phosphinylation

The primary hydroxy groups of head-tail and head-head bis(sugar)-based crow n ethers (1 and 3, respectively) were acylated by (EtO)(2)P(O)Cl and Ph2P(O )Cl in a selective manner. Cation binding ability of the bis-phosphorylated and phosphinylated macrocycles (2 and 4) was evaluated by the picrate extr action method. Introduction of the P-moieties Zed to increase of the extrac tion ability without significant selectivity. (C) 2000 John Wiley & Sons, I nc.