Multi-step reaction with 16 steps
1.1: iodine / 16 h / 20 °C
2.1: sodium cyanide / water / 12 h / 50 °C
2.2: 12 h / 20 °C
3.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.25 h / -30 °C
3.2: 20 h / 20 °C
4.1: acetic acid / water / 3.5 h / 50 °C
5.1: triethylamine; dmap / dichloromethane / 12 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C
7.1: triethyl phosphite / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere
8.1: acetic acid; sodium cyanoborohydride / 0.5 h / 20 °C
9.1: tetrahydrofuran; methanol / 2 h / 20 °C
10.1: potassium carbonate / N,N-dimethyl-formamide
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran
13.1: Dess-Martin periodane / dichloromethane
14.1: diethylamino-sulfur trifluoride / dichloromethane
15.1: hydrogenchloride; methanol / water
16.1: triethylamine; dmap; tert-butyldimethylsilyl chloride / dichloromethane
With
pyridine; hydrogenchloride; methanol; dmap; sodium cyanide; trifluoromethylsulfonic anhydride; diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; iodine; sodium cyanoborohydride; potassium carbonate; Dess-Martin periodane; tert-butyldimethylsilyl chloride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triethyl phosphite;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;