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. 2013 Jul 23;135(30):10898–10901. doi: 10.1021/ja4027727

Scheme 2. Synthesis of Disaccharide 5.

Scheme 2

Reagents and conditions: (a) AcCl, Py, DMAP, CH2Cl2, −40 °C, quant.; (b) (i) TiBr4, CH2Cl2, (ii) 2,4,6-collidine, MeOH, CH2Cl2, 75%; (c) NaOMe, MeOH, −10 °C, 80%; (d) TBSOTf, Py, 0 °C, 92%; (e) HOPO(OBu)2, CH2Cl2, 4 Å MS, quant.; (f) TMSOTf, 7, CH2Cl2, 4 Å MS, 93%; (g) (i) TBAF, AcOH, THF, 0 °C, (ii) Cl3CCN, DBU, CH2Cl2, 0 °C, 89%; (h) BF3·OEt2, 8, CH2Cl2, 4 Å MS, 80%.