تفاعل #74467

معادلة التفاعل

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

compound 5

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

pyridine

phosphorus tribromide

→

title compound

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

المذيبات

ether

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةrefluxed 1 h
2. 2
   درجة الحرارةAfter cooling to room temperature
3. 3
   غسيلwashed with water
4. 4
   استخلاصThe organic extract
5. 5
   تجفيفwas dried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated in vacuo

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)phenyl)methanol (compound 5, 130 g, 195 mmol) from Step 6 in ether (600 mL) at 0° C. was added pyridine (0.79 mL, 9.8 mmol) and phosphorus tribromide (6.4 mL, 68 mmol). The reaction was allowed to slowly warm to room temperature over 15 h and refluxed 1 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water then brine. The organic extract was dried over magnesium sulfate, filtered, and evaporated in vacuo to yield the title compound as a yellow oil, which was used without further purification.

المصدر