(S)-beta-Benzoyloxy-gamma-butyrolactone → 3-O-benzoyl-2-deoxy-threose

Temperatur

-78 °C

To a solution of 101 (0.780 g, 3.8 mmol) in 13 mL dry THF was slowly dropwise added 1.0 M diisopropyl aluminiumhydride (4.7 mL, 4.7 mmol) in toluene at −78° C. The reaction mixture was stirred at −78° C., and as soon as the starting material was completely consumed (TLC, 2 hours), methanol (2 mL) was slowly added in order to quench the reaction. The cooling bath was removed, 15 mL of a saturated aqueous sodium potassium tartrate solution and 25 mL of EtOAc were added and the mixture stirred vigorously for 3 hours. The organic layer was washed with water and brine, and concentrated under vacuo. The residue was purified by chromatography on a silica gel column (n-hexane/EtOAc=8:2) to afford 102 (590 mg, 2.8 mmol) as a colorless oil, in 75% yield, which was characterized as follows:

1. customat −78° C
2. customas soon as the starting material was completely consumed (TLC, 2 hours), methanol (2 mL)
3. additionwas slowly added in order
4. customto quench
5. customthe reaction
6. customThe cooling bath was removed
7. addition15 mL of a saturated aqueous sodium potassium tartrate solution and 25 mL of EtOAc were added
8. stirringthe mixture stirred vigorously for 3 hours
9. washThe organic layer was washed with water and brine
10. concentrationconcentrated under vacuo
11. customThe residue was purified by chromatography on a silica gel column (n-hexane/EtOAc=8:2)

ORD-Eintrag

ord-a2ca14c10a9743c0adbbcee7b1543bc2

Quelldatensatz

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08501709B2