1: nBuLi / tetrahydrofuran / 1.) -70 deg C, 5 min, 2.) RT, 1 h 2: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, 60 deg C, overnight 3: p-TsOH / methanol / 4 h / Ambient temperature 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, from -78 deg C to RT 5: NH2OSO3H / H2O / 2.17 h / 50 °C View Scheme

1: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, 60 deg C, overnight 2: p-TsOH / methanol / 4 h / Ambient temperature 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, from -78 deg C to RT 4: NH2OSO3H / H2O / 2.17 h / 50 °C View Scheme

1: NaH / dimethylformamide / 15.5 h / 80 °C 2: p-TsOH / methanol / 4 h / Ambient temperature 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, from -78 deg C to RT 4: NH2OSO3H / H2O / 2.17 h / 50 °C View Scheme

1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, from -78 deg C to RT 2: NH2OSO3H / H2O / 2.17 h / 50 °C View Scheme

1: Et3N / CH2Cl2 / 1 h 2: NaH / dimethylformamide / 15.5 h / 80 °C 3: p-TsOH / methanol / 4 h / Ambient temperature 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, from -78 deg C to RT 5: NH2OSO3H / H2O / 2.17 h / 50 °C View Scheme

1: p-TsOH / methanol / 4 h / Ambient temperature 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, from -78 deg C to RT 3: NH2OSO3H / H2O / 2.17 h / 50 °C View Scheme

1: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 0.33 h / 0 °C / |Inert atmosphere 2: toluene / 22 h / 20 - 50 °C / |Inert atmosphere View Scheme

1: C6H18NSi2(1-)*Gd(1+); 1,5-anhydro-2,6-dideoxy-3-O-(4,5-difluoro-2-hydroxyphenyl)-6-(diphenylphosphinyl)-D-arabino-hexitol / -30 °C / |Inert atmosphere 2: diisobutylaluminium hydride / toluene / -78 °C / |Inert atmosphere 3: tetrahydrofuran / 0.67 h / -78 °C / |Inert atmosphere 4: tetrabutyl ammonium fluoride / 28 h / 55 °C / |Inert atmosphere 5: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 0.33 h / 0 °C / |Inert atmosphere 6: toluene / 22 h / 20 - 50 °C / |Inert atmosphere View Scheme

1: diisobutylaluminium hydride / toluene / -78 °C / |Inert atmosphere 2: tetrahydrofuran / 0.67 h / -78 °C / |Inert atmosphere 3: tetrabutyl ammonium fluoride / 28 h / 55 °C / |Inert atmosphere 4: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 0.33 h / 0 °C / |Inert atmosphere 5: toluene / 22 h / 20 - 50 °C / |Inert atmosphere View Scheme

1: tetrahydrofuran / 0.67 h / -78 °C / |Inert atmosphere 2: tetrabutyl ammonium fluoride / 28 h / 55 °C / |Inert atmosphere 3: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 0.33 h / 0 °C / |Inert atmosphere 4: toluene / 22 h / 20 - 50 °C / |Inert atmosphere View Scheme