반응 #663544

반응 방정식

alcohol

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

phosphorus tribromide

pyridine

→

bromide

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

용매

ether

반응 조건

후처리

1. 1
   추출The mixture was extracted with EtOAc/H2O (100 mL/150 mL)
2. 2
   건조The combined organic layer was dried over MgSO4
3. 3
   여과filtered
4. 4
   농축concentrated in vacuo
5. 5
   기타The residue was purified by silica gel column chromatography

실험 절차

To a solution of alcohol 105 (5.33 g, 8.01 mmol) in ether (50 mL) were added phosphorus tribromide (0.26 mL, 2.80 mmol) and catalytic amount of pyridine at 0° C. The mixture was allowed to warm to room temperature and stirred at room temperature for 15 hours. The mixture was extracted with EtOAc/H2O (100 mL/150 mL). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the title bromide 106 (4.15 g, 71%).

출처