D-glucose; recombinant Escherichia coli W1485 T=33°C; hydroxylation; pH=6.5 - 7.0; 100 h;

1: 73 percent / N-bromosuccinimide / tetrahydrofuran / 0.33 h / 0 °C 2: 100 percent / K2CO3 / 0.5 h / 0 °C 3: 1) 0.5 N NaOH, 2) dl-10-camphorsulfonic acid / 1) THF, 0 deg C, 14 h, 2) CH2Cl2, RT, 20 h 4: 1) (COCl)2, DMSO, 2) NEt3 / 1a) CH2Cl2, -78 deg C, 15 min, 1b) -45 deg C, 1 h, 2a) -45 deg C, 20 min, 2b) 0 deg C, 15 min 5: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature 6: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h 7: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C 8: CF3COOH / CH2Cl2 / 0.25 h / Ambient temperature View Scheme

1: 100 percent / K2CO3 / 0.5 h / 0 °C 2: 1) 0.5 N NaOH, 2) dl-10-camphorsulfonic acid / 1) THF, 0 deg C, 14 h, 2) CH2Cl2, RT, 20 h 3: 1) (COCl)2, DMSO, 2) NEt3 / 1a) CH2Cl2, -78 deg C, 15 min, 1b) -45 deg C, 1 h, 2a) -45 deg C, 20 min, 2b) 0 deg C, 15 min 4: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature 5: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h 6: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C 7: CF3COOH / CH2Cl2 / 0.25 h / Ambient temperature View Scheme

1: 1) (COCl)2, DMSO, 2) NEt3 / 1a) CH2Cl2, -78 deg C, 15 min, 1b) -45 deg C, 1 h, 2a) -45 deg C, 20 min, 2b) 0 deg C, 15 min 2: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature 3: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h 4: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C 5: CF3COOH / CH2Cl2 / 0.25 h / Ambient temperature View Scheme

1: 1) 0.5 N NaOH, 2) dl-10-camphorsulfonic acid / 1) THF, 0 deg C, 14 h, 2) CH2Cl2, RT, 20 h 2: 1) (COCl)2, DMSO, 2) NEt3 / 1a) CH2Cl2, -78 deg C, 15 min, 1b) -45 deg C, 1 h, 2a) -45 deg C, 20 min, 2b) 0 deg C, 15 min 3: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature 4: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h 5: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C 6: CF3COOH / CH2Cl2 / 0.25 h / Ambient temperature View Scheme

hydrogenchloride in water 0.833333 h; Heating;

D-amino acid oxide ase from pig's kidney

sodium hydroxide; trifluoroacetic acid 1) water, 0 deg C, 14 h, 2) CH2Cl2, 0 deg C, 30 min; Yield given. Multistep reaction;

1: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature 2: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h 3: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C 4: CF3COOH / CH2Cl2 / 0.25 h / Ambient temperature View Scheme

1: H2 / PtO2 2: 2.0 percent Turnov. / aq. HCl / 16 h / Heating View Scheme