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: acetic acid; methanol
12.1: toluene-4-sulfonic acid; trimethyl orthoformate / methanol / 75 °C
13.1: dichloromethane
14.1: toluene-4-sulfonic acid; methanol
15.1: N-ethyl-N,N-diisopropylamine
16.1: 1,1'-Thiocarbonyldiimidazole; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene
With
pyridine; methanol; dmap; sodium cyanide; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; iodine; tri-n-butyl-tin hydride; sodium cyanoborohydride; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-Thiocarbonyldiimidazole; triethyl phosphite; trimethyl orthoformate;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;