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. 2020 Sep 14;63(20):11707–11724. doi: 10.1021/acs.jmedchem.0c00856

Scheme 1. Chemical Synthesis of the (A) LecA-Targeting (11–14) and (B) LecB-Targeting (19) Probes and (C) Alkyne Ciprofloxacin Derivatives 20 and 21.

Scheme 1

Reagents and conditions: (a) p-nitrothiophenol, BF3·Et2O, CH2Cl2, 0 °C to r.t., 16 h; (b) H2, Pd/C, CH2Cl2, r.t., 24 h; (c) (i) Br(CH2)nCOHal, Et3N, or K2CO3, DMF, 0 °C to r.t., 1–4 h, (ii) NaN3, DMF, r.t., 4 h; (d) cat. NaOMe, MeOH, r.t., 1 h; (e) (i) PBr3, CH2Cl2, 0 °C to r.t., 1 h, (ii) HSO3Cl, CH2Cl2, 0 °C to r.t., 3 h; (f) crude 16, K2CO3, DMF, r.t., 5 h; (g) NaN3, DMF, r.t., 5 h; (h) propargylbromide or 4-bromo-but-1-yne, Et3N, DMF, 70 °C, 1–4 d.