تفاعل #74469

معادلة التفاعل

Intermediate 1

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

compound 6

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

→

title compound

المردود 51.0%

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

المردود 51.0%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةto reflux
3. 3
   درجة الحرارةat reflux for 1 h
4. 4
   workup.STIRRINGhad homogenized
5. 5
   workup.STIRRINGstirred overnight at this temperature
6. 6
   أخرىThe resulting solid was isolated by filtration
7. 7
   أخرىdried in vacuo

الإجراء التجريبي

The preceding Intermediate 1 (compound 6, mixture of α,β-anomer in about 1:2 ratio, 105 g, 156 mmol) was slurried in ethanol (1 L) and heated to reflux with stirring. The reaction mixture was held at reflux for 1 h to ensure that all of solution had homogenized; it was then cooled evenly at 15 t/h to ambient temperature and stirred overnight at this temperature. The resulting solid was isolated by filtration and dried in vacuo to yield the title compound (53 g, 79 mmol, 51%) as a white solid.

المصدر