Multi-step reaction with 9 steps
1.1: sulfuric acid / 2 h / 20 °C
1.2: 96 percent / acetone / 72 h / 20 °C
2.1: 61 percent / sodium hydride / dimethylformamide / 3 h / 0 °C
3.1: 92 percent / potassium tert-butoxide / dimethylsulfoxide / 16 h / 100 °C
4.1: ozone / CH2Cl2 / -78 °C
4.2: 95 percent / triphenylphsphine / CH2Cl2 / -78 - 20 °C
5.1: 100 percent / methanol; triethylamine / 16 h / 20 °C
6.1: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C
7.1: 98 percent / imidazole / dimethylformamide / 16 h / 20 °C
8.1: 100 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / -70 - 20 °C
9.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C
9.2: 92 percent / tetrahydrofuran; hexane / 16 h / 20 °C
With
1H-imidazole; methanol; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; potassium tert-butylate; sodium hydride; ozone; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
1.2: Fischer glycosidation / 8.1: Swern oxidation;
DOI:10.1016/j.tetasy.2004.11.069