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. Author manuscript; available in PMC: 2018 Sep 14.
Published in final edited form as: J Med Chem. 2017 Aug 28;60(17):7459–7475. doi: 10.1021/acs.jmedchem.7b00805

Scheme 2.

Scheme 2

Synthesis of Truncated 4′-Thioadenosine Derivatives 3a–d29,a

aReagents and conditions: (a) 2,2-dimethoxypropane, camphosulfonic acid, acetone, rt, 15 h, 95%; (b) NaBH4, EtOH, rt, 2 h, 92%; (c) MsCl, Et3N, CH2Cl2, rt, 1 h, 94%; (d) Na2S, DMF, 80 °C, 15 h, 78%; (e) 60% AcOH, rt, 2 h, 81%; (f) Pb(OAc)4, EtOAc, rt, 15 h, 60%; (g) 6-chloropurine for 13a, 2,6-dichloropurine for 13b, ammonium sulfate, HMDS, 170 °C, 15 h, then TMSOTf, DCE, rt to 80 °C, 3 h; (h) 2 N HCl, THF, rt, 15 h; (i) RNH2, Et3 N, EtOH, rt, 1–3 d.