di-methyltin dichloride; potassium carbonate in tetrahydrofuran T=20°C; Acylation; 12 h;

N-ethyl-N,N-diisopropylamine in chloroform T=-40°C; 4 h; Reagent/catalystTemperatureSolvent; regioselective reaction;

triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran T=0 - 60°C; Mitsunobu reaction; regioselective reaction;

triethylamine in dichloromethane T=20°C;

1: per-O-silylated α-methyl-D-glucopyranoside; benzaldehyde With trimethylsilyl trifluoromethanesulfonate in dichloromethane T=-86°C; 2 h; Molecular sieve; 2: With triethylsilane; 4-methoxy-benzaldehyde; trimethylsilyl trifluoromethanesulfonate in dichloromethane T=-86°C; 5 h; 3: acetic anhydride; benzoyl chloride With tetrabutyl ammonium fluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone Product distribution / selectivity; more than 3 stages;

triethylamine in dichloromethane

1: 75 percent / ZnCl2 / CHCl3 2: 1.) Bu2SnO, 2.) Et3N / 1.) MeOH, benzene, reflux, 2.) 10 deg C to RT View Scheme

1: Me-4,6-(Bz)-α-D-glcp With pyridine in 1,2-dichloro-ethane T=20°C; 1 h; 2: benzoyl chloride in 1,2-dichloro-ethane T=20°C;

1.1: toluene-4-sulfonic acid / aceonitrile / 17 h / Inert atmosphere; Reflux 2.1: di(n-butyl)tin oxide / methanol; toluene / 3 h / Inert atmosphere; Reflux 2.2: 0.5 h / Inert atmosphere; Cooling with ice View Scheme

1: iodine / acetonitrile / 3 h / 20 °C 2: copper dichloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / |Cooling View Scheme