1: 3,6-di-O-benzyl-D-glucal With 4 A molecular sieve; sodium hydrogencarbonate; Dess-Martin periodane in dichloromethane T=20°C; 2: With sodium tetrahydroborate in methanol; dichloromethane T=-5°C; 3: benzyl bromide With sodium hydride in N,N-dimethyl-formamide T=20°C;

water; 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane; tert-butyl alcohol T=0 - 20°C; pH=7; 3 h; aq. phosphate buffer;

1: D-galactal With sodium hydride in N,N-dimethyl-formamide T=20°C; 0.5 h; 2: benzyl bromide in N,N-dimethyl-formamide T=20°C; 24 h;

1: NaOMe / methanol / 5 h / Ambient temperature 2: 1.) (Bu3Sn)2O, 2.) TBABr / 1.) benzene, reflux, 20 h, 2.) benzene, reflux, 17 h View Scheme

tetrabutylammomium bromide; di(n-butyl)tin oxide 1) MeOH, reflux, 5 h, 2) benzene, reflux, 10 h; Yield given. Multistep reaction;

tetrabutylammomium bromide; water; di(n-butyl)tin oxide; triethylamine Yield given. Multistep reaction;

tetrabutylammomium bromide in toluene T=125°C; 0.166667 h; Microwave irradiation;

1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere 2: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / 0 °C 3: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere 4: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 3 h / 0 - 20 °C / pH 7 / aq. phosphate buffer View Scheme

1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere 2: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / 0 °C 3: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere 4: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 3 h / 0 - 20 °C / pH 7 / aq. phosphate buffer View Scheme

1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere 2: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 3 h / 0 - 20 °C / pH 7 / aq. phosphate buffer View Scheme