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. Author manuscript; available in PMC: 2014 Feb 27.
Published in final edited form as: J Am Chem Soc. 2013 Feb 8;135(8):3173–3185. doi: 10.1021/ja311408y

Scheme 3. Synthesis of ThzB19-[A1-GluA4(Oβ ThrB30)-A6-αCOSR.

Scheme 3

(i) TFA for Boc deprotection. Trityl moiety was removed with a cocktail of 95:2.5:2.5 TFA:H2O:triisopropylsilane; (ii) Boc-Xaa-OH, HBTU, DIEA, DMF; (iii) Boc-Glu(Oβ(Alloc-Thr-α-O-cHex))-OH (10), HBTU, DIEA, DMF; (iv) DIEA, DMF, Z(2-Cl)-OSu; (v) Pd(PPh3)4, PhSiH3, DCM; (vi) HF, p-cresol.