Multi-step reaction with 11 steps
1: sulfuric acid / 20 h / Reflux
2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h
3: tetrahydrofuran / 2 h / -78 - 20 °C
4: tetra-n-butylammonium tribromide / dichloromethane; methanol / 3 h / 0 - 20 °C
5: sodium azide / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
6: hydrogenchloride; hydrogen / platinum(IV) oxide / methanol / 5 h / 3361.55 Torr
7: triethylamine / dichloromethane / 1 h / 0 - 20 °C
8: acetic acid / 4 h / Reflux
9: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 16 h
10: tetrabutyl ammonium fluoride / dichloromethane; tetrahydrofuran / 16 h
11: diisopropylamine / dichloromethane / 0.75 h / 20 °C
With
hydrogenchloride; dmap; sodium azide; tetra-n-butylammonium tribromide; di-isopropyl azodicarboxylate; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; diisopropylamine; triphenylphosphine;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;