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. 2019 Oct 10;25(64):14572–14582. doi: 10.1002/chem.201902814

Scheme 1.

Scheme 1

Attempted SPPS of (Thr2, Ser5) analogue 2. Reagents and conditions: (i) HOAt, PyAOP, DIPEA, DMF; (ii) HOAt, PyAOP, DIPEA, DMF, μwave 60 °C for 5 min; (iii) Fmoc deprotection (piperidine, DMF) followed by coupling (Fmoc‐Leu‐OH, HOAt, PyAOP, DIPEA, DMF)×2 (7 a) or coupling Fmoc‐(FmocHmb)Leu‐OH, HBTU, DIPEA, DMF)×2 (7 b); (iv) Fmoc deprotection (piperidine, DMF) followed by coupling (Fmoc‐Ser(tBu)‐OH, HOAt, PyAOP, DIPEA, DMF)×2; (v) Fmoc deprotection (piperidine, DMF) followed by coupling (Fmoc‐Ile‐OH, HOAt, PyAOP, DIPEA, DMF)×2; (vi) Teoc/TMSE deprotection (TBAF, DMF); (vii) Fmoc deprotection (piperidine, DMF).