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. Author manuscript; available in PMC: 2013 Jul 30.
Published in final edited form as: Bioorg Med Chem. 2012 Mar 12;20(9):3009–3015. doi: 10.1016/j.bmc.2012.03.004

Scheme 2.

Scheme 2

Synthesis of 2′-deoxy intermediate 18. Reagents and conditions: (a) MeCN, NaH, 30 min, diiodoimidazole, 24 h, rt ; (b) MeOH, NaOMe; (c) THF, NaH, 3 h, TBAI, PMBCl, 18 h, rt; (d) (i) EtMgBr, THF, 15 min; (ii) anhydrous DMF; (e) (i) NaHCO3, hydroxylamine hydrochloride, H2O; (ii) carbaldehyde, EtOH, rt, 18 h; (f) CDI, THF, reflux, 18 h; (g) NH2C(O)CH2SH, K2CO3, DMF, 60 °C; (h) NaOEt, EtOH.