1: sodium tetrahydroborate 2: water; Candida antarctica lipase B / tert-butyl methyl ether / 0.5 h / 30 °C / |Resolution of racemate; |Enzymatic reaction View Scheme

in water 72 h; Ambient temperatureglucose, bakers'yiest; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

in water 48 h; Ambient temperaturebaker's yeast; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Yield given. Multistep reaction;

1: HN3; Ph3P; diethyl azodicarboxylate / benzene; ethanol / 8 h / 10 - 20 °C 2: Ph3P; H2O / tetrahydrofuran / 18 h 3: 18 percent / tetrahydrofuran / 48 h View Scheme

1: HN3; Ph3P; diethyl azodicarboxylate / benzene; ethanol / 8 h / 10 - 20 °C 2: Ph3P; H2O / tetrahydrofuran / 18 h 3: 18 percent / tetrahydrofuran / 48 h 4: 67 percent / aq. LiOH; H2O2 / methanol / 20 h / 5 °C View Scheme

1: 86.4 percent / Ag2O / Heating 2: 1.5 percent / KOH / ethanol; H2O / 0.75 h / Heating View Scheme

tris-(2-chloro-ethyl)-amine; triphenylphosphine; diethylazodicarboxylate in ethanol; benzene T=10 - 20°C; Substitution; elimination; 8 h;

1: 63 percent / pyridine / 16 h 2: 34 percent / KI / acetone / Heating View Scheme

1: DBU / dimethylsulfoxide / 1 h / 20 °C 2: 22 g / DBU / dimethylsulfoxide / 12 h / 20 °C 3: 90 percent / 3.5 h / 190 °C 4: 82 percent / LiAlH4 / diethyl ether / 0 - 20 °C 5: 92 percent / imidazole / dimethylformamide / 24 h / 20 °C 6: O3; NaOH / methanol; CH2Cl2 / -78 °C 7: 0.98 g / methanol / 0 - 20 °C 8: 84 percent / TBAF / tetrahydrofuran / 0 - 20 °C View Scheme