Reaktion #586907

Reaktionsgleichung

3,4,5-trisbenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-one

2-bromo-1,4-bis(trityloxymethyl)benzene

cyclohexane

sec-butyllithium

→

titled compound

Ausbeute 80.1%

3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-(2,5-bis(trityloxymethyl)phenyl)tetrahydropyran-2-ol

Ausbeute 80.1%

Lösungsmittel

water

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at the same temperature for 30 minutes
2. 2
   Extraktionthe reaction mixture was extracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed with saturated aqueous sodium chloride
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Sonstigeevaporated under reduced pressure
6. 6
   Sonstigeto remove the solvent
7. 7
   SonstigeThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:5))

Vorschrift

Under a nitrogen stream, to a solution of 2-bromo-1,4-bis(trityloxymethyl)benzene (255.3 mg, 0.36 mmol) in toluene (1.5 ml), a cyclohexane solution of sec-butyllithium (0.99 M, 367 μl, 0.36 mmol) was added dropwise at room temperature and the solution was stirred for 30 minutes. This solution was added dropwise at −78° C. to a solution of 3,4,5-trisbenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-one (140 mg, 0.26 mmol) in toluene (1.5 ml) and the mixture was stirred at the same temperature for 30 minutes. After addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then evaporated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:5)) to give the titled compound (242 mg, 80%).

Quelle