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. 2013 Mar 13;23(9):2555–2559. doi: 10.1016/j.bmcl.2013.02.117

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Copyright © 2013 Published by Elsevier Ltd.

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Scheme 4 — Synthesis of 2,2-difluoro-2-deoxyribose-1-phosphate prodrugs. (a) LiAl(OtBu)₃H, THF/H₂O 4:1, −78 °C, 2 h, (b) TIPS-OTf, 2,6-lutidine, CH₂Cl₂, 0 °C, 2 h, 67% over 2 steps, (c) Et₃N, H₂O, MeOH, rt, 4 days, 70%, (d) CbzCl, DMAP, CH₂Cl₂, rt, 12 h, 100%, (e) HF-pyr, pyridine, rt, 100%, (f) appropriate phosphorochloridate, tBuMgCl, THF, rt, 15 h, (g) H₂, Pd/C, EtOH, rt, 2 h.