تفاعل #74466

معادلة التفاعل

(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

المردود 98.5%

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

المردود 98.5%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter removal of organic volatiles under reduced pressure
2. 2
   أخرىthe residue was partitioned between ethyl acetate and saturated ammonium chloride solution
3. 3
   أخرىThe organic layer was separated
4. 4
   استخلاصthe aqueous layer was extracted with ethyl acetate
5. 5
   غسيلThe combined organic layers were washed with brine
6. 6
   تجفيفdried over magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىThe crude residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes)

الإجراء التجريبي

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.

المصدر