Multi-step reaction with 9 steps
1.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / Reflux; Inert atmosphere
1.2: 70 h / Reflux
1.3: Inert atmosphere
2.1: guanidine nitrate; sodium methylate / methanol; dichloromethane / 0.5 h / 20 °C / Inert atmosphere
3.1: pyridine / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
4.1: sodium azide; 15-crown-5 / N,N-dimethyl-formamide / 23 h / 20 - 50 °C / Inert atmosphere
5.1: sodium hydroxide; trimethylphosphane / water; tetrahydrofuran / 21 h / 20 °C / Cooling with ice; Inert atmosphere
6.1: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere
7.1: boron trichloride / 1,2-dichloro-ethane; dichloromethane; hexane / 17 h / -78 - 20 °C / Inert atmosphere
8.1: 15-crown-5 / N,N-dimethyl-formamide / 23 h / 20 - 90 °C / Inert atmosphere
9.1: sodium hydroxide / water; 1,4-dioxane / 2 h / 0 °C / Inert atmosphere
With
pyridine; sodium azide; N,O-bis-(trimethylsilyl)-acetamide; 15-crown-5; sodium methylate; guanidine nitrate; boron trichloride; sodium hydroxide; trimethylphosphane;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
1.1: |Vorbrueggen Nucleoside Synthesis;
DOI:10.1021/jo4022937