Multi-step reaction with 12 steps
1.1: 5.70 g / pyridine / 6 h / 20 °C
2.1: DIPEA / CH2Cl2 / 24 h / 20 °C
3.1: 0.444 g / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C
4.1: pyridine / 0.17 h / 20 °C
5.1: NaH / tetrahydrofuran / 2 h / 0 °C
5.2: tetrahydrofuran / 1.33 h / 0 °C
6.1: 0.359 g / aq. AcOH / 1.17 h / 20 °C
7.1: 100 percent / water / 22 h / Heating
8.1: 78 percent / K2CO3 / methanol / 14 h / 20 °C
9.1: 95 percent / pyridine / 4 h / 20 °C
10.1: 100 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C
11.1: 2,4,6-triisopropylbenzenesulfonyl chloride; pyridine / 1 h / 20 °C
11.2: 69 percent / pyridine / 1 h / 20 °C
12.1: 75 percent / aq. AcOH / 7 h / 20 °C
With
pyridine; 2,4,6-triisopropylphenylsulfonyl chloride; tetrabutyl ammonium fluoride; water; sodium hydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja050732x