반응 #2293915

반응 방정식

alcohol

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

benzoyl chloride

→

title compound

수율 91.7%

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

수율 91.7%

용매

pyridine

반응 조건

후처리

1. 1
   세척The mixture was washed with aq. saturated NaHCO3 solution
2. 2
   건조The 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
6. 6
   기타to provide

실험 절차

To a solution of alcohol 103 (9.9 g, 14.88 mmol) in pyridine (36 mL) was added benzoyl chloride (1.9 mL, 16.37 mmol) at room temperature. The mixture was stirred at room temperature for 6 hours. The mixture was washed with aq. saturated NaHCO3 solution. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the mixture of anomers of the title compound (10.5 g). The anomeric mixture of 104 was recrystallized with IPA (150 mL). The precipitate was collected by filtration and washed with cold IPA (50 mL) and dried under high vacuum to obtain β-anomer of the title compound 104 (6.13 g, 54%).

출처