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. Author manuscript; available in PMC: 2018 Jan 18.
Published in final edited form as: J Am Chem Soc. 2017 May 10;139(22):7595–7602. doi: 10.1021/jacs.7b02396

Figure 2.

Figure 2

Synthesis of AZ-BPS and BPS. Reagents and conditions: (i) 1,2-dibromoethane, K2CO3, acetonitrile (MeCN), reflux, 6 h, 65%; (ii) CH3(OCH2CH2)3OTs, K2CO3, DMF, reflux, 12 h, 90%; (iii) propargylamine, HATU, TEA, DIPEA, DMF, room temperature (rt), 24 h, 70%; (iv) NBS, DCM, rt, 0.5 h, 95%; (v) 9, Mg(ClO4)2, piperidine, toluene, reflux, 24 h, 31%; (vi) 10, trifluoroacetic acid (TFA), DCM, rt, 12 h; chloranil, BF3·O(C2H5)2, TEA, 1 h, 45%; (vii) NaN3, DMF, 130 °C, 12 h, 91%; (viii) NBS, DCM, rt, 0.5 h, 96%; (ix) 9, Mg(ClO4)2, piperidine, toluene, reflux, 24 h, 44%; (x) 7, CuSO4·5H2O, sodium ascorbate, DMF/MeOH/H2O, 57%.