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. Author manuscript; available in PMC: 2018 Oct 15.
Published in final edited form as: Bioorg Med Chem. 2017 Aug 3;25(20):5433–5440. doi: 10.1016/j.bmc.2017.07.063

Scheme 3.

Scheme 3

Synthesis of ribose-ketal analogs: Reagents and conditions: (a) TBSCl, imid., DMF, rt, 2–24 h; (b) CH2Br2, NaOH, TBAB, CH2Cl2/H2O, 40 °C, 72 h; (c) Boc2O, DMAP, DMF, 18 h; (d) TBAF, THF, 1–18 h; (e) MsCl, Et3N, CH2Cl2, 1 h; (f) MeNH2/EtOH, THF, 50 °C, 18 h; (g) 13, Et3N, NaI, MeCN, rt, 3–18 h; (h) 1M H2SO4, MeOH, rt, 18 h; (i) cyclohexanone, TFA, rt; (j) TFA, CH2Cl2, rt, 1 h.