1: methyl 1-thio-β-L-fucopyranoside With sodium hydride in N,N-dimethyl-formamide; paraffin oil T=0°C; 1 h; 2: benzyl bromide in N,N-dimethyl-formamide; paraffin oil T=0 - 20°C; 24 h;

1: 56 percent / SnCl4 / 1,2-dichloro-ethane / 4 h / 20 °C 2: MeOH, NaOMe / 4 h / 20 °C 3: 1.) NaH / 1.) DMF, 30 min, 20 deg C 2.) DMF, 16 h, 20 deg C View Scheme

1: MeOH, NaOMe / 4 h / 20 °C 2: 1.) NaH / 1.) DMF, 30 min, 20 deg C 2.) DMF, 16 h, 20 deg C View Scheme

N-bromosuccinmide; water in acetone T=20°C; 3 h; optical yield given as percent de;

1: 79 percent / tetrabutylammonium bromide, CuBr2, molecular sieve 4A / 1,2-dichloro-ethane; dimethylformamide / 16 h / Ambient temperature 2: 70 percent / 60percent aq. acetic acid / 1.5 h / 50 °C 3: 4-toluenesulfonic acid monohydrate / benzene / 1.5 h / Ambient temperature 4: 80percent aq. acetic acid / 1 h / Ambient temperature 5: 79 percent / SO3-pyridine complex / dimethylformamide / 1.5 h / Ambient temperature 6: 0.1 M sodium methoxide / methanol / 16 h / Ambient temperature 7: H2 / 10percent Pd-C / aq. ethanol / 48 h / 2587.7 Torr View Scheme