Scheme 29.
Reaction conditions: (a) Benzyl((bis(benzyloxy)phosphoryl)methyl)-phosphonochloridate, KHMDS, THF, –78°C → rt, O/N; (b) Sodium methoxide, MeOH, rt, O/N, then p-toluenesulfonic acid, H2O, (CH3)2CO, O/N; (c) reagent 167, MeCN, 1H-tetrazole, 0°C→rt, 1.5 days, then 3-chloroperoxybenzoic acid, MeCN, 0°C→rt, 3 h; (d) H2, Palladium black, NaHCO3, t-BuOH/H2O, rt, O/N; (e) NH3(aq) conc, 4 days, then H+-Dowex.