Reaktion #6157

Reaktionsgleichung

benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyldimethylsilyl)oxy]-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate

tetrabutylammonium fluoride trihydrate

→

benzyl (2S,3S,5R)-2-hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate

Ausbeute 60.4%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter evaporation the residue
2. 2
   workup.DISSOLUTIONwas dissolved in 50 ml of ether
3. 3
   Waschenwashed with water
4. 4
   SonstigeThe ethereal phase was dried
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe product was chromatographed on silica gel

Vorschrift

M)g) 480 mg benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyldimethylsilyl)oxy]-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate and 350 mg of tetrabutylammonium fluoride trihydrate were dissolved in 8 ml of THF and stirred for 12 hours. After evaporation the residue was dissolved in 50 ml of ether and washed with water. The ethereal phase was dried and evaporated. The product was chromatographed on silica gel. There was obtained 240 mg of benzyl (2S,3S,5R)-2-hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate, MS: 463 [(M+H)+ -dihydro-2H-pyran-2-yl].

Quelle