반응 #6157

반응 방정식

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

수율 60.4%

용매

THF

반응 조건

후처리

1. 1
   기타After evaporation the residue
2. 2
   workup.DISSOLUTIONwas dissolved in 50 ml of ether
3. 3
   세척washed with water
4. 4
   기타The ethereal phase was dried
5. 5
   기타evaporated
6. 6
   기타The product was chromatographed on silica gel

실험 절차

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].

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