Multi-step reaction with 19 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
2.1: 1,1,3,3-Tetramethyldisiloxane / (Ph3P)2IrCl(CO) / toluene / 2 h / 20 °C
3.1: hydroquinone / acetonitrile / 95 °C
4.1: methyl p-toluene sulfonate / water / 2 h / 110 °C
4.2: 4 h / 95 °C
5.1: hydrogen / rhodium contaminated with carbon / tetrahydrofuran / 7 h / 20 °C / 760.05 Torr
6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
7.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C
7.2: Cooling with ice
8.1: triphenylphosphine / dichloromethane / 0.33 h / Cooling with ice
8.2: 0.33 h / Cooling with ice
9.1: n-butyllithium / tetrahydrofuran / -78 - 0 °C
10.1: sodium hydrogencarbonate; Dess-Martin periodane / chloroform
11.1: sodium carbonate / ethanol / 1.5 h / 80 °C
12.1: Iodine monochloride / dichloromethane / 2 h / 0 - 20 °C
13.1: potassium phosphate / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 80 °C
14.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.67 h / 0 - 70 °C
15.1: sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 1.67 h / 20 °C / Phosphate buffer
16.1: potassium carbonate / N,N-dimethyl-formamide / 1.33 h / 20 °C
17.1: trifluoroacetic acid / chloroform / 2.67 h / 20 - 50 °C
18.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
19.1: hydrogen bromide; acetic acid / water / 1.5 h / 20 - 50 °C
With
sodium hypochlorite; sodium chlorite; potassium phosphate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,1,3,3-Tetramethyldisiloxane; tetrabutyl ammonium fluoride; hydrogen bromide; hydrogen; Iodine monochloride; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; hydroquinone; methyl p-toluene sulfonate; triphenylphosphine; trifluoroacetic acid;
bis-triphenylphosphine-palladium(II) chloride; rhodium contaminated with carbon; (Ph3P)2IrCl(CO);
In
tetrahydrofuran; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile;