Multi-step reaction with 12 steps
1.1: sulfuric acid / N,N-dimethyl-formamide / 20 °C
2.1: sodium hydride / N,N-dimethyl-formamide
2.2: 4 h / 20 °C
3.1: hydrogenchloride; water / methanol / 4 h / 20 °C
4.1: sodium periodate / ethanol; water; methanol / 3 h / 20 °C
5.1: copper(II) bis(trifluoromethanesulfonate); borane-THF / 2 h / 20 °C / Inert atmosphere
6.1: 1H-imidazole; dmap / dichloromethane / 24 h / 20 °C / Inert atmosphere
7.1: pyridine / dichloromethane / 1 h / -15 °C / Inert atmosphere
8.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C
9.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C
9.2: 4 h / 20 °C
10.1: pyridine / 2 h / 0 - 20 °C
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
12.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / Inert atmosphere
12.2: 0.75 h / -78 - 20 °C / Inert atmosphere
With
pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium periodate; sodium azide; borane-THF; oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; water; copper(II) bis(trifluoromethanesulfonate); sodium hydride; dimethyl sulfoxide; triphenylphosphine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
9.1: |Staudinger Azide Reduction / 9.2: |Staudinger Azide Reduction / 12.1: |Swern Oxidation / 12.2: |Swern Oxidation;
DOI:org/10.1016/j.tetlet.2012.08.143