تفاعل #74494

معادلة التفاعل

(2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)naphthalen-1-yl)-tetrahydro-2H-pyran

potassium cyanide

→

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

المردود 46.0%

المذيبات

EtOH

water

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was refluxed overnight
2. 2
   استخلاصextracted with EtOAc
3. 3
   غسيلThe organic layer was washed with brine
4. 4
   تجفيفdried over anhydrous MgSO4
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated in vacuo
7. 7
   أخرىThe crude residue was purified by column chromatography

الإجراء التجريبي

To a solution of the (2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)naphthalen-1-yl)-tetrahydro-2H-pyran in EtOH (80 mL) and water (40 mL) was added potassium cyanide (4.24 g, 65.1 mmol). The reaction mixture was refluxed overnight. After cooling to room temperature, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The crude residue was purified by column chromatography to yield 2-(4-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxy-methyl)-tetrahydro-2H-pyran-2-yl)naphthalen-2-yl)acetonitrile (10.9 g, 46%) as a white solid.

المصدر