Fig. 5: Synthetic routes of pentamer G5 with the S(ha)R(ple)SS configuration. | Nature Synthesis

Fig. 5: Synthetic routes of pentamer G5 with the S(ha)R(ple)SS configuration.

From: Synthesis of chiral sequence-defined oligomers via sulfur–fluoride and sulfur–phenolate exchange reactions

Fig. 5

Reaction conditions: (i) A1 (1 equiv.), 1d (3 equiv.), DBU (1.5 equiv.), LiBr (3 equiv.), THF, r.t., 2 h; (ii) G1 (1 equiv.), phenol (1.2 equiv.), LiBr (1.5 equiv.), DBU (1.2 equiv.), THF, r.t., 2 h; (iii) G2 (1 equiv.), ammonium molybdate tetrahydrate (0.1 equiv.), 30% H2O2 (18 equiv.), THF, r.t., 2 h; (iv) G3 (1 equiv.), bisphenol A (5 equiv.), DBU (5 equiv.), THF, r.t., 2 h; (v) G4 (1 equiv.), G1 (1 equiv.), LiBr (1.6 equiv.), DBU (1.2 equiv.), THF, r.t., 3 h. SuFEx, sulfur–fluoride exchange reaction; SuPhenEx, sulfur–phenolate exchange reaction; THF, tetrahydrofuran; DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene; tol, p-tolyl.

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