1: 1.) BH3-SMe2, trimethylsilyl trifluoromethanesulfonate, 2.) potassium hydroden carbonate / 1.) dichloromethane, -20 - -10 deg C, 0.2 h, 2.) ethanol, water, 55-65 deg C, 1 h 2: 1.) sodium azide, ammonium chloride, 2.) trimethylphosphine / 1.) ethanol, water, 70-75 deg C, 18 h, 2.) acetonitrile, <38 deg C, 2 h 3: sodium azide, ammonium chloride / dimethylformamide / 18 h / 70 - 80 °C 4: 0.98 kg / sodium bicarbonate / hexane / 1 h 5: 1.) hydrogen, 2.) phophoric acid / 1.) Raney nickel / 1.) ethanol, 16 h, 2.) ethanol, 55 65 deg C View Scheme

phosphoric acid in ethanol T=55°C; 0.5 h;

1: triethylamine / dichloromethane / 0.17 h / 0 °C 2: sodium azide / water; N,N-dimethyl-formamide / 18 h / 90 °C 3: hydrogen / ethanol / 18 h / 20 °C 4: phosphoric acid / ethanol / 0.5 h / 55 °C View Scheme

1.1: copper(II) bis(trifluoromethanesulfonate); borane-THF / 2 h / 20 °C / |Inert atmosphere 2.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C / |Inert atmosphere 3.1: pyridine / dichloromethane / 1 h / -15 °C / |Inert atmosphere 4.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C 5.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 5.2: 4 h / 20 °C 6.1: pyridine / 2 h / 0 - 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / |Inert atmosphere 8.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere 8.2: 0.75 h / -78 - 20 °C / |Inert atmosphere 9.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / |Inert atmosphere 9.2: 2 h / 0 °C / |Inert atmosphere 10.1: 10 Pd/C; hydrogen / ethanol / 96 h / 20 °C 11.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 12.1: triethylamine / dichloromethane / 0.75 h / 0 °C 13.1: sodium azide / ethanol; water / 8 h / |Reflux 14.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 14.2: Staudinger Azide Reduction / 24 h / 20 °C 15.1: 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 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: sodium hydride / N,N-dimethyl-formamide 1.2: 4 h / 20 °C 2.1: hydrogenchloride; water / methanol / 4 h / 20 °C 3.1: sodium periodate / ethanol; water; methanol / 3 h / 20 °C 4.1: copper(II) bis(trifluoromethanesulfonate); borane-THF / 2 h / 20 °C / |Inert atmosphere 5.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C / |Inert atmosphere 6.1: pyridine / dichloromethane / 1 h / -15 °C / |Inert atmosphere 7.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C 8.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 8.2: 4 h / 20 °C 9.1: pyridine / 2 h / 0 - 20 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / |Inert atmosphere 11.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere 11.2: 0.75 h / -78 - 20 °C / |Inert atmosphere 12.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / |Inert atmosphere 12.2: 2 h / 0 °C / |Inert atmosphere 13.1: 10 Pd/C; hydrogen / ethanol / 96 h / 20 °C 14.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 15.1: triethylamine / dichloromethane / 0.75 h / 0 °C 16.1: sodium azide / ethanol; water / 8 h / |Reflux 17.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 17.2: Staudinger Azide Reduction / 24 h / 20 °C 18.1: phosphoric acid / ethanol / 0 - 50 °C View Scheme

1.1: hydrogenchloride; water / methanol / 4 h / 20 °C 2.1: sodium periodate / ethanol; water; methanol / 3 h / 20 °C 3.1: copper(II) bis(trifluoromethanesulfonate); borane-THF / 2 h / 20 °C / |Inert atmosphere 4.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C / |Inert atmosphere 5.1: pyridine / dichloromethane / 1 h / -15 °C / |Inert atmosphere 6.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C 7.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 7.2: 4 h / 20 °C 8.1: pyridine / 2 h / 0 - 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / |Inert atmosphere 10.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere 10.2: 0.75 h / -78 - 20 °C / |Inert atmosphere 11.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / |Inert atmosphere 11.2: 2 h / 0 °C / |Inert atmosphere 12.1: 10 Pd/C; hydrogen / ethanol / 96 h / 20 °C 13.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 14.1: triethylamine / dichloromethane / 0.75 h / 0 °C 15.1: sodium azide / ethanol; water / 8 h / |Reflux 16.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 16.2: Staudinger Azide Reduction / 24 h / 20 °C 17.1: phosphoric acid / ethanol / 0 - 50 °C View Scheme

1.1: sodium periodate / ethanol; water; methanol / 3 h / 20 °C 2.1: copper(II) bis(trifluoromethanesulfonate); borane-THF / 2 h / 20 °C / |Inert atmosphere 3.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C / |Inert atmosphere 4.1: pyridine / dichloromethane / 1 h / -15 °C / |Inert atmosphere 5.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C 6.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 6.2: 4 h / 20 °C 7.1: pyridine / 2 h / 0 - 20 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / |Inert atmosphere 9.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere 9.2: 0.75 h / -78 - 20 °C / |Inert atmosphere 10.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / |Inert atmosphere 10.2: 2 h / 0 °C / |Inert atmosphere 11.1: 10 Pd/C; hydrogen / ethanol / 96 h / 20 °C 12.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 13.1: triethylamine / dichloromethane / 0.75 h / 0 °C 14.1: sodium azide / ethanol; water / 8 h / |Reflux 15.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 15.2: Staudinger Azide Reduction / 24 h / 20 °C 16.1: phosphoric acid / ethanol / 0 - 50 °C View Scheme

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Reflux 2.1: potassium carbonate / 5 h / 20 °C 3.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 6.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 6.2: 1 h 7.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 8.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 8.2: 0.5 h / -78 °C / Inert atmosphere 8.3: 0.5 h 9.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 10.1: triphenylphosphine / toluene / 3 h / Reflux 11.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 20 °C 12.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 13.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 13.2: 4 °C View Scheme

1.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 4.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 4.2: 1 h 5.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 6.2: 0.5 h / -78 °C / Inert atmosphere 6.3: 0.5 h 7.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 8.1: triphenylphosphine / toluene / 3 h / Reflux 9.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 20 °C 10.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 11.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 11.2: 4 °C View Scheme