반응 #74466

반응 방정식

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

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

tetrabutylammonium fluoride

→

title compound

수율 98.5%

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

수율 98.5%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타After removal of organic volatiles under reduced pressure
2. 2
   기타the residue was partitioned between ethyl acetate and saturated ammonium chloride solution
3. 3
   기타The organic layer was separated
4. 4
   추출the aqueous layer was extracted with ethyl acetate
5. 5
   세척The combined organic layers were washed with brine
6. 6
   건조dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타The crude residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes)

실험 절차

To a solution of (2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxy-methyl)tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane (198 mmol) from Step 5 in tetrahydrofuran (500 mL) was added tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 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 ethyl acetate and saturated ammonium chloride solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes) to yield the title compound (130 g, 195 mmol, 98%, mixture of α,β-anomer in about 1:2 ratio) as a white solid.

출처