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. 2024 Nov 28;146(49):33675–33711. doi: 10.1021/jacs.4c11556

Scheme 2. Synthesis of Trifunctional Linkers 53–57.

Scheme 2

Reaction conditions: (a) MEMCl or MOMBr, DIPEA, DCM, r.t., 16 h; (b) MsCl, DIPEA, DCM, r.t., 3 h; (c) (i) NaH, DMF, 0 °C, 30 min, (ii) 6 or 7, DMF, 60 °C, 16 h; (d) (i) NaH, DMF, 0 °C, 30 min, (ii) 39 or 40, DMF, 60 °C, 16 h; (e) (i) NaH, DMF, 0 °C, 30 min, (ii) 38, DMF, 60 °C, 16 h; (f) OsO4, NaIO4, 2,6-lutidine, dioxane, H2O, r.t., 16 h; (h) 2-methyl-2-butene, NaH2PO4, NaClO2, t-BuOH, H2O, r.t., 16 h.

Products 43–47 formed through step (f) then (g).

Product 47 formed directly from step (e).