Multi-step reaction with 7 steps
1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 17 h / 60 °C
2.1: bis(tri-t-butylphosphine)palladium(0); cesium fluoride / 1,4-dioxane / 16 h / 50 °C / Inert atmosphere
3.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 20 °C
4.1: sodium periodate / water; acetone / 20 °C
5.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.5 h / Inert atmosphere
5.2: 0.5 h
6.1: 1,8-diazabicyclo[5.4.0] undec-7-ene; diphenyl phosphoryl azide / 1,4-dioxane / 70 °C
7.1: hydrogen; pyrographite; palladium / 1,4-dioxane / 16 h / 20 °C / 760.05 Torr
With
sodium periodate; osmium(VIII) oxide; bis(tri-t-butylphosphine)palladium(0); diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0] undec-7-ene; hydrogen; pyrographite; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; palladium; 4-methylmorpholine N-oxide; lithium tri-t-butoxyaluminum hydride; triethylamine; cesium fluoride;
In
tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ml200252b