Synthesis of novel chiral macrocyclic ligands bearing methyl 4,6-O-benzylidene-α-D-mannopyranoside

Abstract

O-Alkylation of methyl 4,6-O-benzylidene-α-D-mannopyranoside with t-butyl bromoacetate under phase-transfer conditions, followed by reduction and tosylation leads to an intermediate which was used in the formation of the two diaza-crown ethers (3a) and (3b)via condensation with 1,8-diamino-3,6-dioxaoctane in the presence of KF–Al₂O₃ and N,N-bisethoxycarbonyl-1,8-diamino-3,6-dioxaoctane in Me₂SO–NaH–KBr, respectively.