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. 2019 Feb 13;10(3):306–311. doi: 10.1021/acsmedchemlett.8b00508

Scheme 2. Synthesis of Phosphate Prodrug (32).

Scheme 2

Conditions: (a) LAH, Et2O, 0 °C (90%); (b) HCl, dioxane, rt (99%); (c) 6, Hunig’s base, DMA, 100 °C (95%); (d) PhB(OH)2, X-Phos, Pd(OAc)2, 2 M K3PO4, 100 °C (73%.); (e) (i) dibenzyl diisopropylphosphoramidite, tetrazole, DCM/THF, 0 °C; (ii) 30% H2O2, 0 °C (73%); (f) (i) H2, Pd/C, EtOH (74%); (ii) NaHCO3, MeOH/H2O (99%).