Yield given. Multistep reaction;

1: 1,2-diamino-benzene With acetic acid in water 0.5 h; 2: D-(+)-mannose 2 h; Reflux;

1.1: sulfuric acid / N,N-dimethyl-formamide / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide 2.2: 4 h / 20 °C 3.1: hydrogenchloride; water / methanol / 4 h / 20 °C 4.1: sodium periodate / ethanol; water; methanol / 3 h / 20 °C 5.1: copper(II) bis(trifluoromethanesulfonate); borane-THF / 2 h / 20 °C / |Inert atmosphere 6.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C / |Inert atmosphere 7.1: pyridine / dichloromethane / 1 h / -15 °C / |Inert atmosphere 8.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C 9.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 9.2: 4 h / 20 °C 10.1: pyridine / 2 h / 0 - 20 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / |Inert atmosphere 12.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere 12.2: 0.75 h / -78 - 20 °C / |Inert atmosphere 13.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / |Inert atmosphere 13.2: 2 h / 0 °C / |Inert atmosphere 14.1: 10 Pd/C; hydrogen / ethanol / 96 h / 20 °C 15.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 16.1: triethylamine / dichloromethane / 0.75 h / 0 °C 17.1: sodium azide / ethanol; water / 8 h / |Reflux 18.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 18.2: Staudinger Azide Reduction / 24 h / 20 °C 19.1: phosphoric acid / ethanol / 0 - 50 °C View Scheme

1.1: sulfuric acid / N,N-dimethyl-formamide / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide 2.2: 4 h / 20 °C 3.1: hydrogenchloride; water / methanol / 4 h / 20 °C 4.1: sodium periodate / ethanol; water; methanol / 3 h / 20 °C 5.1: copper(II) bis(trifluoromethanesulfonate); borane-THF / 2 h / 20 °C / |Inert atmosphere 6.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C / |Inert atmosphere 7.1: pyridine / dichloromethane / 1 h / -15 °C / |Inert atmosphere 8.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C 9.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 9.2: 4 h / 20 °C 10.1: pyridine / 2 h / 0 - 20 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / |Inert atmosphere 12.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere 12.2: 0.75 h / -78 - 20 °C / |Inert atmosphere 13.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / |Inert atmosphere 13.2: 2 h / 0 °C / |Inert atmosphere 14.1: 10 Pd/C; hydrogen / ethanol / 96 h / 20 °C 15.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 16.1: triethylamine / dichloromethane / 0.75 h / 0 °C 17.1: sodium azide / ethanol; water / 8 h / |Reflux View Scheme

sodium azide in phosphate buffer T=37°C; pH=7.4; 100 h;

sodium azide in phosphate buffer T=37°C; pH=7.4; Kinetics;

bei der Einw. von gewissen Pentosen vergaerenden und aus Fructose Mannit bildenen Bakterien, insbesondere der Gruppe Lactobacillus pentoaceticus n.sp.,;

sodium tetrahydroborate in water T=20°C; 2 h;

Na[H2B(CN)2] in trifluoroacetic acid T=100°C; 40 h;

sodium cyanoborohydride; triethylamine in methanol; water T=80°C; Reduction; amination; pH=6.2; 72 h;