1: potassium carbonate / tetrahydrofuran / 7 h / 20 °C 2: lead; zinc; iodine / tetrahydrofuran / -15 - 20 °C / Inert atmosphere 3: ammonium formate / palladium on carbon / toluene / 3 h / 80 °C View Scheme

1.1: magnesium / tert-butyl methyl ether / 4 h / 55 °C 1.2: -10 - 0 °C 1.3: 3 h / 25 - 50 °C 2.1: sodium hydroxide / dimethyl sulfoxide / 5 h / 25 - 30 °C 3.1: water; lithium chloride; sodium tetrahydroborate / isopropyl alcohol / 20 h / -5 - 30 °C 3.2: pH 1 4.1: sodium hydrogencarbonate / toluene / 24 h / -15 °C / Enzymatic reaction 5.1: sodium hydrogencarbonate; iodine / ethyl acetate / 5 h / -15 °C 6.1: dimethyl sulfoxide / 24 h / 25 - 90 °C 6.2: 3 h / 25 - 30 °C 7.1: hydrogenchloride / tert-butyl methyl ether; acetone / 0.5 h / 25 - 30 °C 8.1: triethylamine / dichloromethane / 1 h / 12 - 22 °C 8.2: 4 h / 12 - 25 °C 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

sodium hydroxide in tetrahydrofuran; diethyl ether

1: NaBH4 / methanol 2: NH3 / ethanol View Scheme