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. Author manuscript; available in PMC: 2020 May 31.
Published in final edited form as: Bioorg Med Chem. 2016 Mar 3;24(8):1718–1728. doi: 10.1016/j.bmc.2016.02.044

Scheme 2.

Scheme 2.

Synthesis of di- and tri-sulfonaphthyl tyrosine sulfate mimetics. Reagents and conditions: (a) (1) HBF4, H2O, 0 °C, 1 h; (2) NaNO2, H2O, 0 °C, 10 min; (b) NaOAc, DMF/H2O (1:1), 0 °C, 10 min; (c) thiosemicarbazide, AcOH, 70 °C, 4 h; (d) n-Bu4NI(cat), DMF.