반응 #2130088

반응 방정식

(2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane

tetrabutylammonium fluoride

→

titled compound

수율 98.0%

(2-Chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxy-methyl)-tetrahydro-2H-pyran-2-yl)phenyl)methanol

수율 98.0%

용매

THF

반응 조건

후처리

1. 1
   기타After removal of organic volatiles under reduced pressure
2. 2
   기타the residue was partitioned between EtOAc and saturated ammonium chloride
3. 3
   기타The organic layer was separated
4. 4
   추출the aqueous layer was extracted with EtOAc
5. 5
   세척The combined organic layers were washed with brine
6. 6
   건조dried over anhydrous MgSO4
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타The crude residue was purified on column chromatography

실험 절차

To a solution of (2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane in THF (500 mL) was added tetrabutylammonium fluoride (1.0 M in THF, 594 mL, 594 mmol) and the reaction mixture stirred at ambient temperature for 2 h. After removal of organic volatiles under reduced pressure, the residue was partitioned between EtOAc and saturated ammonium chloride. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude residue was purified on column chromatography to provide the titled compound (168 g, 98%, ca. 2:1 mixture of anomers (β:α)) as a white solid.

출처