Multi-step reaction with 6 steps
1: imidazole / dimethylformamide / Ambient temperature
2: DMAP, Et3N / CH2Cl2 / 24 h
3: 60 percent / AIBN / toluene / 24 h / 80 °C
4: 35 percent / OsO4, NaIO4 / dioxane; H2O / 6 h / Ambient temperature
5: 1.) pyridinium dichromate, 2.) NaOH / 1.) MeOH, DMF, RT, overnight, 2.) MeOH, RT, overnight
6: 1.) N-methylmorpholine, O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate, 1-hydroxybenzotriazole, 2.) N-methylmorpholine / 1.) DMF, RT, 2 h, 2.) DMF
With
4-methyl-morpholine; 1H-imidazole; dmap; sodium hydroxide; sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; 2,2'-azobis(isobutyronitrile); benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine;
In
1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0960-894X(99)00052-9