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Synthesis of phosphoramidite 145. (a) B(OCH3)3, CH(OCH3)3, Na2CO3, MeOH, 150 °C; (b) I2, (0.6 equiv), CAN (0.5 equiv), AcOH, 80 °C; (c) TBDMSCl (3.5 equiv), imidazole (5 equiv), DMF; (d) 5 mol % Pd(CH3CN)2Cl2, Bu3SnCH=CH2, CH3CN, 80 °C; (e) OsO4, NMO (2.5 equiv), acetone H2O t-BuOH (4:1:1); (f) Ac2O (4 equiv), pyridine; (g) TBAF (2 equiv), AcOH (2 equiv), THF; (h) DMTrCl (1.5 equiv), pyridine; (i) [(iPr)2N]2POCH2CH2CN (1.8 equiv), DCI (0.7 equiv), CH3CN CH2Cl2 (1:10).
