1: (S)-(-)-2-methyl-CBS-oxazaborolidine / tetrahydrofuran / 1 h / 0 °C 2: 99 percent / i-Pr2NEt / CH2Cl2 / 0.5 h / 0 °C 3: 100 percent / aq. LiOH / tetrahydrofuran / 48 h / Ambient temperature 4: Et3N / toluene / 2 h / Ambient temperature 5: DMAP / toluene / 12 h / 50 °C 6: 76 percent / DDQ / CH2Cl2; H2O / 1.5 h / Ambient temperature 7: 87 percent / TPAP, NMO, MS4A / acetonitrile / 1 h / Ambient temperature 8: 1.) NBS, 2.) CrO3, H2SO4 / 1.) THF, phosphate buffer pH 7, 0 deg C, 15 min, 2.) acetone, 0 deg C, 15 min 9: MS 4A, PPC / CH2Cl2 / 12 h / Ambient temperature 10: HF*pyridine / tetrahydrofuran / Ambient temperature View Scheme

1: 100 percent / aq. LiOH / tetrahydrofuran / 48 h / Ambient temperature 2: Et3N / toluene / 2 h / Ambient temperature 3: DMAP / toluene / 12 h / 50 °C 4: 76 percent / DDQ / CH2Cl2; H2O / 1.5 h / Ambient temperature 5: 87 percent / TPAP, NMO, MS4A / acetonitrile / 1 h / Ambient temperature 6: 1.) NBS, 2.) CrO3, H2SO4 / 1.) THF, phosphate buffer pH 7, 0 deg C, 15 min, 2.) acetone, 0 deg C, 15 min 7: MS 4A, PPC / CH2Cl2 / 12 h / Ambient temperature 8: HF*pyridine / tetrahydrofuran / Ambient temperature View Scheme

1: 99 percent / i-Pr2NEt / CH2Cl2 / 0.5 h / 0 °C 2: 100 percent / aq. LiOH / tetrahydrofuran / 48 h / Ambient temperature 3: Et3N / toluene / 2 h / Ambient temperature 4: DMAP / toluene / 12 h / 50 °C 5: 76 percent / DDQ / CH2Cl2; H2O / 1.5 h / Ambient temperature 6: 87 percent / TPAP, NMO, MS4A / acetonitrile / 1 h / Ambient temperature 7: 1.) NBS, 2.) CrO3, H2SO4 / 1.) THF, phosphate buffer pH 7, 0 deg C, 15 min, 2.) acetone, 0 deg C, 15 min 8: MS 4A, PPC / CH2Cl2 / 12 h / Ambient temperature 9: HF*pyridine / tetrahydrofuran / Ambient temperature View Scheme