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. 2014 Sep 25;57(19):8056–8071. doi: 10.1021/jm500946r

Scheme 4. Initial Attempts toward the Synthesis of αGlcN(1↔1)αMan Scaffold.

Scheme 4

Reagents and conditions: (a) 1. HF·Py, THF, 2. Ac2O, DMAP, pyridine, 85%; (b) NBS, acetone–H2O, 24:1, 0 °C, 89%; (c) CCl3CN, DBU, CH2Cl2, 67%; (d) TMSOTf (0.05 equiv), 4 Å MS, CH2Cl2, 0 °C; (e) (CF3CO)2O, CF3COOH, Et3SiH, CH2Cl2, 0 °C, 91%; (f) 1. (BnO)2PN(iPr)2, 1H-tetrazole, CH2Cl2, 2. mCPBA, −78 °C, 91%; (g) 1. Zn, AcOH, CH2Cl2, 0 °C, 2. FmocCl, EtN(iPr)2, CH2Cl2, 88%; (h) 1. [Ir(COD)(Ph2MeP)2]PF6, H2, THF, 2. I2, aq. THF, 86%.