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. Author manuscript; available in PMC: 2023 Jan 5.
Published in final edited form as: ChemMedChem. 2021 Oct 22;17(1):e202100568. doi: 10.1002/cmdc.202100568

Scheme 2.

Scheme 2.

Synthesis of ANPs 8, the corresponding phosphorodiamidate prodrugs 9, and phosphono disphosphates 10. Reagents and conditions: a) LDA, THF, −20 °C, then oxirane, THF, 10 °C, then TfOCH2P(O)(OiPr)2, −40 °C; b) XPhos Pd G2, R-B(OH)2, K3PO4, THF/H2O (4:1), 40 °C, then TFA, RT, 5 min; c) TMSBr, pyridine, RT, then (L)-NH2CH(Bn)COOiPr·HCl, Aldrithiol™, PPh3, Et3N, pyridine, 70 °C; d) (i) TMSBr, pyridine, RT, (ii) 2M aq. TEAB and TBAH, (iii) CDI, (Bu3N)2P2O7, DMSO.