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. Author manuscript; available in PMC: 2013 Apr 26.
Published in final edited form as: J Med Chem. 2012 Apr 13;55(8):3945–3959. doi: 10.1021/jm300165m

Scheme 1a.

Scheme 1a

Synthesis of ortho-substituted biphenyl mannosides

a. Reagents and conditions: (a) BF3-Et2O, CH2Cl2, reflux; (b) 3-substituted phenyl boronic acid derivatives, Cat. Pd(PPh3)4, Cs2CO3, dioxane/water(5/1), 80 °C; (c) Cat. MeONa, MeOH, rt; (d) MeNH2/EtOH, rt; (e) bis(pinacolato)diboron, Cat. Pd(dppf)Cl2, KOAc, DMSO, 80 °C.