تفاعل #74468

معادلة التفاعل

(2S,3R,4R,5S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)-4-chlorophenyl)-tetrahydro-2H-pyran

(2S,3R,4R,5S)-3,4,5-Tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)-4-chlorophenyl)-tetrahydro-2H-pyran

potassium cyanide

ethyl acetate

→

title compound

المردود 80.0%

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

المردود 80.0%

المذيبات

ethanol

water

water

—

hexanes

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was refluxed overnight
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   غسيلThe organic layer was washed with brine
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated in vacuo

الإجراء التجريبي

To a solution of (2S,3R,4R,5S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)-4-chlorophenyl)-tetrahydro-2H-pyran (195 mmol) from Step 7 in ethanol (260 mL) and water (130 mL) was added potassium cyanide (31.8 g, 488 mmol). The reaction mixture was refluxed overnight. After cooling to room temperature, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. Flash chromatography on a Biotage® apparatus (silica gel, 5 to 40% ethyl acetate in hexanes gradient) gave the title compound (105 g, 156 mmol, 80%, mixture of α,β-anomer in about 1:2 ratio) as a colorless oil.

المصدر