Multi-step reaction with 11 steps
1: RuCl3, NaIO4 / CCl4; acetonitrile; various solvent(s) / 19 h / 35 °C
2: 2.) CSA, molecular sieves 4A / 1.) THF, 23 deg C, 1 h, 2.) CHCl3, 10 min
3: 95 percent / OsO4 / tetrahydrofuran; pyridine / 20 h / 23 °C
4: SO3*pyridine, DMSO, Et3N / CH2Cl2 / 1 h / 23 °C
5: 100 percent / silica gel / 11 h / 23 °C
6: DMAP / CH2Cl2 / 21 h / 23 °C
7: AcOH / H2O / 19 h / 35 °C
8: 1.) pyridinium dichromate (PDC), 2.) KMnO4, NaH2PO4 / 1.) CH2Cl2, 23 deg C, 22 h, 2.) t-BuOH, H2O, 20 min
9: 93 percent / K2CO3, MeOH / 4 h / 23 °C
10: 91 percent / PhSO2Cl, pyridine / toluene / 9 h / 23 °C
11: 99 percent / 2 M aq. HCl / 1,2-dimethoxy-ethane / 2 h / 80 °C
With
pyridine; hydrogenchloride; methanol; dmap; ruthenium trichloride; potassium permanganate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; dipyridinium dichromate; pyridine-SO3 complex; 4 A molecular sieve; camphor-10-sulfonic acid; silica gel; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; benzenesulfonyl chloride;
In
tetrahydrofuran; pyridine; tetrachloromethane; 1,2-dimethoxyethane; dichloromethane; water; toluene; acetonitrile;