Fig. 3: Synthetic scheme for building blocks L1, L2, and their protected variants. | Nature Communications

Fig. 3: Synthetic scheme for building blocks L1, L2, and their protected variants.

From: Paramagnetic encoding of molecules

Fig. 3

Conditions: (i) BnBr (benzyl bromide), TEA (triethylamine), THF (tetrahydrofurane); (ii) PPh3, THF, 0 °C followed by DIAD (diisopropyl azodicarboxylate), MeI, 0 °C → RT; (iii) (PhSe)2, EtOH, NaBH4, 0 °C; (iv) H2O2, THF, 0 °C → RT; (v) MCPBA (meta-chloroperoxybenzoic acid), CHCl3, 85 °C; (vi) cyclen, t-BuOH, 105 °C; (vii) t-BuO2CCH2Br, K2CO3, MeCN; (viii) H2, Pd@C, AcOH, MeOH; (ix) TFA; (x) FmocCl, aq. borate/NaOH buffer (pH 9.0), MeCN; (xi) MeO2CCH2Br, K2CO3, MeCN; (xii) Ac2O, TEA, DMAP (4-dimethylaminopyridine), MeCN. Intermediates in brackets were not isolated. Colors define stereochemistry of the hydroxyproline moiety: 2R,3S,4S (green) and 2S,3R,4S (violet). Detailed synthetic procedures are provided in Supplementary Figs. 22–36.

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