copper(l) chloride 1.) CHCl3, 15 d, r.t.; 2.) CHCl3, 2 d, r.t.; Yield given. Multistep reaction. Yields of byproduct given;

copper(l) chloride 1.) CHCl3, 5 d, r.t.; 2.) CHCl3, 2 d, r.t.; Yield given. Multistep reaction. Yields of byproduct given;

1: 90.3 percent / KOH; PEG-600 / tetrahydrofuran / 20 °C 2: 97.5 percent / AcOH / H2O / 18 h / 25 °C 3: 99.5 percent / silica gel-supported NaIO4 / CH2Cl2 / 1.5 h / 0 °C View Scheme

1: 80 percent / Collins' reagent / CH2Cl2 / 0.5 h / Ambient temperature 2: gl. AcOH, water / 4 h / 60 °C 3: 61 percent / pyridine / 10 h / Ambient temperature 4: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 5: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C 6: 12 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature View Scheme

1: 80 percent / Collins' reagent / CH2Cl2 / 0.5 h / Ambient temperature 2: gl. AcOH, water / 4 h / 60 °C 3: 61 percent / pyridine / 10 h / Ambient temperature 4: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 5: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C 6: 12 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 7: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme

1: 90.3 percent / KOH; PEG-600 / tetrahydrofuran / 20 °C 2: 97.5 percent / AcOH / H2O / 18 h / 25 °C View Scheme

1: diacetone D-mannose With sodium hydride in tetrahydrofuran T=0°C; 0.666667 h; Inert atmosphere; 2: benzyl bromide in tetrahydrofuran T=20°C; Inert atmosphere;

potassium hydroxide; 18-crown-6 ether in tetrahydrofuran 0.25 h; Ambient temperature;

sodium hydride in N,N-dimethyl-formamide 2 h; Ambient temperature;

1: 78 percent / methyltri-n-octylammonium chloride, 10M NaOH / benzene / 30 h / Ambient temperature 2: 94 percent / 12M HCl / methanol; H2O / 7 h / Ambient temperature 3: 66 g / pyridine / 18 h / 25 °C View Scheme