Multi-step reaction with 9 steps
1: 96 percent / potassium tert-butoxide, 18-crown-6 / tetrahydrofuran / 1 h
2: OsO4, N-methylmorpholine-N-oxide / acetone; H2O
3: NaIO4 / dioxane; H2O / 25 h
4: NaBH4 / tetrahydrofuran; propan-2-ol / 1 h / 0 deg C to room temperature
5: 100 percent / pyridine / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) room temperature, 1 h
6: 98 percent / NaN3 / dimethylsulfoxide / 1.83 h / 60 °C
7: 100 percent / 0.5 M aq. HCl / methanol / 1.17 h / Heating
8: 1.) methyl dichlorophosphate, pyridine, 2.) 2.0 M HCl / 1.) 80 min, 2.) water (pH 1)
9: hydrogen, NaHCO3 / 10 percent Pd-C / H2O; tetrahydrofuran; ethanol / 42 h / 2585.7 Torr
With
pyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium azide; 18-crown-6 ether; potassium tert-butylate; hydrogen; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; methyl dichlorophosphoridate;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; isopropyl alcohol; acetone;
DOI:10.1016/0040-4020(91)80004-L