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Synthesis of non-hydrolysable PP-IP analogues. Reagents and conditions: (i) (bis-benzyloxyphosphoryl-methyl)phosphoryl chloride, KHMDS, THF, −78 °C to rt, overnight; (ii) NaOMe, MeOH, rt, overnight; (iii) H2O, p-TsOH, acetone, overnight; (iv) N,N-diethyl-1,5-dihydro-2,4,3-benzodioxaphosphepin-3-amine, 1H-tetrazole, CH3CN, 0 °C to rt, 36 h; (v) mCPBA, CH3CN, 0 °C to rt, 3 h; (vi) H2, Pd black, NaHCO3, t-BuOH/H2O, rt, overnight; (vii) Conc. aq. NH3, rt, 4 d; (viii) Dowex-H+.
