WbnJ protein; manganese (II) chloride; DL-threo-1,4-dimercapto-2,3-butanediol; tris(hydroxymethyl)methylamine hydrochloride pH=7.5; 72 h;

bovine testes β-galactosidase; McIlvain buffer in water T=37°C; pH=4.3; 50 h;

sodium in methanol 1.5 h;

potassium phosphate buffer; Bacillus circulanus (bgaC-gene) β-galactosidase in water; N,N-dimethyl-formamide T=37°C; pH=6.0; 4.5 h; Title compound not separated from byproducts;

1.1: 62.8 percent / ammonium carbonate / dimethylformamide / 22 h / 30 °C 2.1: 83.9 percent / Cs2CO3 / CH2Cl2 / 30 h / 20 °C 3.1: molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 1.5 h / 20 °C 3.2: 66.2 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 0.25 h / -18 °C 4.1: acetic acid; H2O / 45 °C 5.1: pyridine 6.1: 89.7 percent / Na / methanol / 1.5 h View Scheme

1.1: 83.9 percent / Cs2CO3 / CH2Cl2 / 30 h / 20 °C 2.1: molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 1.5 h / 20 °C 2.2: 66.2 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 0.25 h / -18 °C 3.1: acetic acid; H2O / 45 °C 4.1: pyridine 5.1: 89.7 percent / Na / methanol / 1.5 h View Scheme

1.1: molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 1.5 h / 20 °C 1.2: 66.2 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 0.25 h / -18 °C 2.1: acetic acid; H2O / 45 °C 3.1: pyridine 4.1: 89.7 percent / Na / methanol / 1.5 h View Scheme

1.1: 92.3 percent / Na / 0.5 h 2.1: 95.9 percent / Na / methanol / 0.5 h 3.1: 50.7 percent / ZnCl2 / 108 h / 20 °C 4.1: molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 1.5 h / 20 °C 4.2: 66.2 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 0.25 h / -18 °C 5.1: acetic acid; H2O / 45 °C 6.1: pyridine 7.1: 89.7 percent / Na / methanol / 1.5 h View Scheme

1.1: 50.7 percent / ZnCl2 / 108 h / 20 °C 2.1: molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 1.5 h / 20 °C 2.2: 66.2 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 0.25 h / -18 °C 3.1: acetic acid; H2O / 45 °C 4.1: pyridine 5.1: 89.7 percent / Na / methanol / 1.5 h View Scheme

1.1: molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 1.5 h / 20 °C 1.2: 66.2 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 0.25 h / -18 °C 2.1: acetic acid; H2O / 45 °C 3.1: pyridine 4.1: 89.7 percent / Na / methanol / 1.5 h View Scheme