1: 85 percent / n-BuLi / tetrahydrofuran / 5 h 2: 2.) HgO, BF3*Et2O / 1.) pyridine, RT, 12 h, 2.) THF, H2O, 23 deg C, 4 h 3: 1.) D-glucose, 2.) 2N NaOH / 1.) bakers' yeast, ethanol, water, 25-28 deg C, 12 h, 2.) methanol, 12 h 4: 1.) HIO4*2H2O, 2.) NaBH4 / 1.) THF, 23 deg C, 2 min, 2.) EtOH, 23 deg C, 12 h View Scheme

n-butyllithium; potassium tert-butylate 1.) THF, -40 deg C, 2.) THF, -40 deg C, 2 h, than warming up to r.t.; Yield given. Multistep reaction;

Multi-step reaction with 2 steps 1: 85 percent / n-BuLi / tetrahydrofuran / 5 h2: 2.) HgO, BF3*Et2O / 1.) pyridine, RT, 12 h, 2.) THF, H2O, 23 deg C, 4 h  

Multi-step reaction with 3 steps 1: 85 percent / n-BuLi / tetrahydrofuran / 5 h2: 2.) HgO, BF3*Et2O / 1.) pyridine, RT, 12 h, 2.) THF, H2O, 23 deg C, 4 h3: 1.) D-glucose, 2.) 2N NaOH / 1.) bakers' yeast, ethanol, water, 25-28 deg C, 12 h, 2.) methanol, 12 h