Multi-step reaction with 10 steps
1.1: Iodine monochloride / 1,2-dichloro-ethane / 3 h / 70 °C / Inert atmosphere
2.1: sodium nitrite; sulfuric acid / ethanol / 0 °C / Reflux
3.1: tin(II) chloride dihdyrate; ethanol / Reflux
4.1: sodium azide; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; copper(l) iodide; N,N`-dimethylethylenediamine / dimethyl sulfoxide; water / 1 h / 20 °C
5.1: sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; copper(ll) sulfate pentahydrate / ethanol; water / 12 h / 20 °C
6.1: dicyclohexyl-carbodiimide / dichloromethane / 0.17 h
6.2: 0.5 h
7.1: sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; copper(II) sulfate / water; tetrahydrofuran / 12 h / 20 °C
8.1: dicyclohexyl-carbodiimide / dichloromethane / 0.17 h
8.2: 0.5 h
9.1: copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 5 h / 20 °C
10.1: trimethylaluminum / toluene / 20 °C
10.2: 2 h / 20 - 100 °C
With
copper(l) iodide; sodium azide; copper(ll) sulfate pentahydrate; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; tin(II) chloride dihdyrate; ethanol; sulfuric acid; trimethylaluminum; Iodine monochloride; copper(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; N,N`-dimethylethylenediamine; sodium nitrite;
In
tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; toluene;
DOI:10.1002/ejoc.201301838