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. 2011 Mar 15;2(5):331–336. doi: 10.1021/ml100253p

Scheme 2. Synthesis of C-4′′-Ether Linked Macrolides by HBTU-Mediated Coupling of Carboxylic Acid 11 with Selected Amines (Chart 1).

Scheme 2

Reagents and conditions: (a) allyl-tert-butylcarbonate, Pd(Ph3P)4, THF, reflux, 3 h; (b) MeOH, rt, 20 h; (c) OsO4, NaIO4, THF, rt, 3 h; (d) R1NH2, NaBH3CN or NaBH(OAc)3, AcOH, MeOH, rt, 3 h; or HCO2H, EtOAc, reflux, 5 h; (e) LiOH, THF/H2O, rt, 12 h.