Multi-step reaction with 9 steps
1.1: acetic acid / dichloromethane / 0.5 h / 40 °C / Inert atmosphere
1.2: 16 h / 20 °C
2.1: tetrahydrofuran / 16 h / 15 - 20 °C / Inert atmosphere
3.1: acetic acid / 27 h / 92 °C / Inert atmosphere
4.1: trichlorophosphate / toluene; N,N-dimethyl-aniline / 16 h / 110 °C / Inert atmosphere
4.2: 25 °C / pH 12
5.1: 2,4,6-Triisopropylbenzenesulfonyl azide; potassium tert-butylate / 2-methyltetrahydrofuran / 3.5 h / -50 - -40 °C / Inert atmosphere; 3 ? Molecular sieve
5.2: 36 h / -20 - 30 °C
5.3: pH 8
6.1: hydrogen / platinum(IV) oxide / 1,4-dioxane / 3 h / 7500.75 Torr / Autoclave
7.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane / 3.75 h / 80 °C / Inert atmosphere
8.1: hydrogenchloride / 1,4-dioxane / 12 h / 18 - 23 °C / Inert atmosphere
9.1: sodium hydrogencarbonate; 3,5-dichlorosalicyclaldehyde; (2R,3R)-2,3-bis(benzyloxy)tartaric acid / dichloromethane; water; Isopropyl acetate / 3 h / 70 °C
With
hydrogenchloride; 2,4,6-Triisopropylbenzenesulfonyl azide; potassium tert-butylate; (2R,3R)-2,3-bis(benzyloxy)tartaric acid; hydrogen; sodium hydrogencarbonate; sodium carbonate; acetic acid; trichlorophosphate; 3,5-dichlorosalicyclaldehyde;
platinum(IV) oxide; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 2-methyltetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; Isopropyl acetate; water; acetic acid; N,N-dimethyl-aniline; toluene;