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(a) Structure of an influenza endo-nuclease inhibitor. (b) Synthesis of inhibitor building blocks. (c) Synthesis of bi-functional small molecules.
Reagents and conditions: (a) para-methoxybenzyloxyamine, toluene, reflux; (b) trifloroacetic acid, DCM; (c) i) (Boc)2O, Et3N, DMF, H2O, 60 °C; ii) TPS-Cl, pyridine, r.t.; iii) Cysteamine hyrochloride, Cs2CO3, DMF; (d) 6-azido-hexanoic acid, EDCI, TEA, DCM; (e) i) CuSO4, sodium ascorbate, DMSO/H2O; ii) trifloroacetic acid, DCM.
