pyridine; dichlorotriphenylphosphorane in acetonitrile T=20°C; 3.5 h;

glucose dehydrogenase; D-glucose in phosphate buffer; dimethyl sulfoxide T=37 - 39°C; pH=6.9; 0.666667 h;

sodium tetrahydroborate in ethylene glycol dimethyl ether; water T=-78°C; 0.233333 h; Cooling with acetone-dry ice;

pyridine; dichlorotriphenylphosphorane in acetonitrile T=23°C; 1 h;

pyridine; pyridinium poly(hydrogen fluoride) in tetrahydrofuran T=0 - 20°C; Inert atmosphere;

D-glucose; nicotinamide adenine dinucleotide; glucose dehydrogenase; ketoreductase KRED-EXP-C1A in water; dimethyl sulfoxide T=32 - 39°C; pH=6.9; 0.67 - 4 h; Enzymatic reactionphosphate buffer; Product distribution / selectivity;

1: With pyridine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride in dichloromethane T=23°C; 1 h; 2: With pyridine; dichlorotriphenylphosphorane in dichloromethane; acetonitrile T=23°C; 1 h;

1.1: H2 / Pd/C / ethanol / 12 h / 23 °C / 760 Torr 2.1: 2.68 g / Dess-Martin reagent / CH2Cl2 / 1 h / 23 °C 3.1: 83 percent / tetrahydrofuran / 5 h / -78 °C 4.1: 92 percent / KHCO3; KF; aq. H2O2 / methanol; tetrahydrofuran / 18 h / 23 °C 5.1: 83 percent / aq. ceric ammonium nitrate / acetonitrile / 1 h / 0 °C 6.1: aq. LiOH / tetrahydrofuran / 96 h / 5 °C 7.1: bis(2-oxo-3-oxazolidinyl)phosphonic chloride; pyridine / CH2Cl2 / 1 h / 23 °C 7.2: 100 mg / pyridine; PPh3Cl2 / acetonitrile; CH2Cl2 / 1 h / 23 °C View Scheme

1.1: 89 percent / tributyltin hydride; AIBN / benzene / 4 h / 80 °C 2.1: H2 / Pd/C / ethanol / 12 h / 23 °C / 760 Torr 3.1: 2.68 g / Dess-Martin reagent / CH2Cl2 / 1 h / 23 °C 4.1: 83 percent / tetrahydrofuran / 5 h / -78 °C 5.1: 92 percent / KHCO3; KF; aq. H2O2 / methanol; tetrahydrofuran / 18 h / 23 °C 6.1: 83 percent / aq. ceric ammonium nitrate / acetonitrile / 1 h / 0 °C 7.1: aq. LiOH / tetrahydrofuran / 96 h / 5 °C 8.1: bis(2-oxo-3-oxazolidinyl)phosphonic chloride; pyridine / CH2Cl2 / 1 h / 23 °C 8.2: 100 mg / pyridine; PPh3Cl2 / acetonitrile; CH2Cl2 / 1 h / 23 °C View Scheme

sodium tetrahydroborate; lithium chloride in ethylene glycol dimethyl ether; water T=10°C; 0.166667 h;