Synthesis of a C3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues

A C-3-symmetric macrocycle with alternating sugar amino acid and tyrosine residues was synthesized in seven steps from tyrosine tert-butyl ester and a sugar amino acid precursor derived from D-glucosamine. An Fmoc-protected D-glucosamine derivative was oxidized at C-6 to give the sugar amino acid, which was immediately coupled to tyrosine tert-butyl ester to produce an orthogonally protected building block. This building block was Subsequently elongated to the trimer via the dimer, and finally cyclized to give the C-3-symmetric macrocycle. (C) 2004 Elsevier Ltd. All rights reserved.