1: sodium cyanoborohydride; alpha-hydroxyethanoic acid / methanol / 20 °C / |Inert atmosphere; |Large scale 2: ammonia / methanol / 22 h / 70 °C / 4897.34 Torr / |Sealed tube; |Large scale 3: hydrogenchloride / isopropyl alcohol / 4 h / 50 °C / |Large scale 4: benzotriazol-1-ol; 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; ethyl acetate; 1-methyl-pyrrolidin-2-one / 16 h / 20 - 24 °C 5: acetic acid; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; NaMnO4 / tert-butyl methyl ether; water / 12 °C View Scheme

1: ammonia / methanol / 22 h / 70 °C / 4897.34 Torr / |Sealed tube; |Large scale 2: hydrogenchloride / isopropyl alcohol / 4 h / 50 °C / |Large scale 3: benzotriazol-1-ol; 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; ethyl acetate; 1-methyl-pyrrolidin-2-one / 16 h / 20 - 24 °C 4: acetic acid; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; NaMnO4 / tert-butyl methyl ether; water / 12 °C View Scheme

1.1: zinc; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 70 °C / |Inert atmosphere; |Large scale 1.2: 1 h / 20 °C / |Large scale 2.1: sulfuryl dichloride / tert-butyl methyl ether / 1.5 h / 20 - 23 °C / |Large scale 3.1: triethylamine / N,N-dimethyl-formamide / 14 h / 55 °C / |Inert atmosphere; |Large scale 4.1: ammonium acetate / propan-1-ol; ethanol / 1 h / 50 °C / |Inert atmosphere; |Large scale 5.1: sodium cyanoborohydride; alpha-hydroxyethanoic acid / methanol / 20 °C / |Inert atmosphere; |Large scale 6.1: ammonia / methanol / 22 h / 70 °C / 4897.34 Torr / |Sealed tube; |Large scale 7.1: hydrogenchloride / isopropyl alcohol / 4 h / 50 °C / |Large scale 8.1: benzotriazol-1-ol; 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; ethyl acetate; 1-methyl-pyrrolidin-2-one / 16 h / 20 - 24 °C 9.1: acetic acid; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; NaMnO4 / tert-butyl methyl ether; water / 12 °C View Scheme

1.1: dimethyl sulfoxide / 4.67 h / 85 °C / |Inert atmosphere; |Large scale 2.1: zinc; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 70 °C / |Inert atmosphere; |Large scale 2.2: 1 h / 20 °C / |Large scale 3.1: sulfuryl dichloride / tert-butyl methyl ether / 1.5 h / 20 - 23 °C / |Large scale 4.1: triethylamine / N,N-dimethyl-formamide / 14 h / 55 °C / |Inert atmosphere; |Large scale 5.1: ammonium acetate / propan-1-ol; ethanol / 1 h / 50 °C / |Inert atmosphere; |Large scale 6.1: sodium cyanoborohydride; alpha-hydroxyethanoic acid / methanol / 20 °C / |Inert atmosphere; |Large scale 7.1: ammonia / methanol / 22 h / 70 °C / 4897.34 Torr / |Sealed tube; |Large scale 8.1: hydrogenchloride / isopropyl alcohol / 4 h / 50 °C / |Large scale 9.1: benzotriazol-1-ol; 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; ethyl acetate; 1-methyl-pyrrolidin-2-one / 16 h / 20 - 24 °C 10.1: acetic acid; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; NaMnO4 / tert-butyl methyl ether; water / 12 °C View Scheme

1.1: triethylamine / dichloromethane / 4.17 h / -10 - -5 °C / |Large scale 2.1: dimethyl sulfoxide / 4.67 h / 85 °C / |Inert atmosphere; |Large scale 3.1: zinc; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 70 °C / |Inert atmosphere; |Large scale 3.2: 1 h / 20 °C / |Large scale 4.1: sulfuryl dichloride / tert-butyl methyl ether / 1.5 h / 20 - 23 °C / |Large scale 5.1: triethylamine / N,N-dimethyl-formamide / 14 h / 55 °C / |Inert atmosphere; |Large scale 6.1: ammonium acetate / propan-1-ol; ethanol / 1 h / 50 °C / |Inert atmosphere; |Large scale 7.1: sodium cyanoborohydride; alpha-hydroxyethanoic acid / methanol / 20 °C / |Inert atmosphere; |Large scale 8.1: ammonia / methanol / 22 h / 70 °C / 4897.34 Torr / |Sealed tube; |Large scale 9.1: hydrogenchloride / isopropyl alcohol / 4 h / 50 °C / |Large scale 10.1: benzotriazol-1-ol; 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; ethyl acetate; 1-methyl-pyrrolidin-2-one / 16 h / 20 - 24 °C 11.1: acetic acid; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; NaMnO4 / tert-butyl methyl ether; water / 12 °C View Scheme

1: sulfuryl dichloride / tert-butyl methyl ether / 1.5 h / 20 - 23 °C / |Large scale 2: triethylamine / N,N-dimethyl-formamide / 14 h / 55 °C / |Inert atmosphere; |Large scale 3: ammonium acetate / propan-1-ol; ethanol / 1 h / 50 °C / |Inert atmosphere; |Large scale 4: sodium cyanoborohydride; alpha-hydroxyethanoic acid / methanol / 20 °C / |Inert atmosphere; |Large scale 5: ammonia / methanol / 22 h / 70 °C / 4897.34 Torr / |Sealed tube; |Large scale 6: hydrogenchloride / isopropyl alcohol / 4 h / 50 °C / |Large scale 7: benzotriazol-1-ol; 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; ethyl acetate; 1-methyl-pyrrolidin-2-one / 16 h / 20 - 24 °C 8: acetic acid; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; NaMnO4 / tert-butyl methyl ether; water / 12 °C View Scheme

1: hydrogenchloride / isopropyl alcohol / 6 h / 60 - 65 °C 2: N-ethyl-N,N-diisopropylamine; HATU / acetonitrile / 5 h / 25 - 30 °C 3: Dess-Martin periodane / dichloromethane / 0 - 30 °C View Scheme

1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0 - 30 °C 2: hydrogenchloride / isopropyl alcohol / 6 h / 60 - 65 °C 3: N-ethyl-N,N-diisopropylamine; HATU / acetonitrile / 5 h / 25 - 30 °C 4: Dess-Martin periodane / dichloromethane / 0 - 30 °C View Scheme

1: N-ethyl-N,N-diisopropylamine; HATU / acetonitrile / 5 h / 25 - 30 °C 2: Dess-Martin periodane / dichloromethane / 0 - 30 °C View Scheme