Réaction #169650

Équation de réaction

potassium dihydrogen phosphate

phosphoric acid

benzyl [(3S)-4-oxotetrahydro-2H-pyran-3-yl]carbamate

NaOH

glucose

NADP

→

benzyl [(3S,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]carbamate

Solvants

water

Conditions de réaction

Traitement

1. 1
   FiltrationA white solid was collected via filtration
2. 2
   Lavagewashed 2× with water (200 mL)
3. 3
   Températurecooled to rt
4. 4
   FiltrationA white solid was collected via filtration
5. 5
   Lavagewashed with toluene (200 mL)

Mode opératoire

To a solution of potassium dihydrogen phosphate (62.7 g, 0.461 mol) in 3.6 L of water was added phosphoric acid to pH=7.0. To this solution was added glucose (112 g, 0.622 mol), NADP (3.6 g), GDH-103 (1.8 g), KRED 119 (3.6 g), and crude benzyl [(3S)-4-oxotetrahydro-2H-pyran-3-yl]carbamate (103.4 g, 0.4148 mol). After 17 h, the reaction was adjusted to pH 6.5 with 5 N NaOH. A white solid was collected via filtration and washed 2× with water (200 mL). The solid was suspended in 600 mL of toluene and stirred with an overhead stirrer at 105° C. for 1 h, then cooled to rt. A white solid was collected via filtration and washed with toluene (200 mL) to provide benzyl [(3S,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]carbamate.

Source