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

Scheme 2. Synthesis of Glucosamine Lactol Acceptors 8 and 10.

Scheme 2

Reagents and conditions: (a) Ac2O, DMAP, pyridine, 97%; (b) Et3SiH, TfOH, 4 Å MS, −78 °C, CH2Cl2, 68%; (c) 1. (BnO)2PN(iPr)2, 1H-tetrazole, CH2Cl2, 2. mCPBA, −78 °C, 90%; (d) HF·Py, THF, 91% for 8, 94% for 10; (e) 1. Zn, AcOH, CH2Cl2, 2. FmocCl, EtN(iPr)2, CH2Cl2, 89%.