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. 2011 May 18;2(8):614–619. doi: 10.1021/ml200098j

Scheme 1. Synthesis of Diaminocyclitol 1.

Scheme 1

Reagents and conditions: (a) LiAlH4, THF, rt, 91%. (b) Boc2O, Et3N, CH2Cl2, rt, 82%. (c) MsCl, Et3N, THF, rt, 63%. (d) NaN3, DMF, 90 °C, 65%. (e) CF3CO2H, CH2Cl2, rt, 86%. (f) C8H17CHO, NaBH3CN, AcOH (cat.), MeOH, rt, 75%. (g) Pd/C, MeOH, HCl, H2 (2 atm), rt, 77%.