boron trichloride in dichloromethane 2.5 h; Ambient temperature;

hydrogen; palladium on activated charcoal in ethyl acetate

1: With sodium hydroxide T=80°C; 2: With sodium cyanoborohydride in tetrahydrofuran Further byproducts given;

1: 1.63 g / aluminium chloride / diethyl ether / 1.5 h / 15 °C / < 15 deg C 2: 490 mg / H2 / 5percent palladium-charcoal / ethyl acetate View Scheme

D-glucose in aq. phosphate buffer pH=7; Enzymatic reaction;

1: L. Horner, W. Duerckheimer, K. H. Weber, K. Doelling, Chem. Ber. 97, 312 (1964) 2: boron trichloride View Scheme

boron trichloride

1: 10.6 g / pyridine / 3.25 h / 80 - 90 °C 2: 12.52 g / N-bromosuccinimide / CCl4 / 0.58 h / Heating 3: acetonitrile / 2 h / Heating 4: triethylamine / toluene / 1.) reflux, 4 h, 2.) room temperature, 12 h 5: 90 percent / LiALH4 / diethyl ether / 0.75 h / Ambient temperature 6: 73 percent / potassium nitrosodisulphonate, AcONa / H2O; methanol / 0.5 h View Scheme

pyridine T=80 - 90°C; 3.25 h;

1: 10.6 g / pyridine / 3.25 h / 80 - 90 °C 2: 12.52 g / N-bromosuccinimide / CCl4 / 0.58 h / Heating View Scheme