Реакция #82472

Уравнение реакции

water

L-Fucose tetraacetate

Ethyl 3-(2-hydroxyphenyl)benzyloxyacetate

boron trifluoride etherate

→

ethyl 3-(2-(2,3,4-tri-O acetyl-α-L-fucopyranosyloxy)phenyl)benzyloxyacetate

Выход 61.0%

Растворители

1,2-dichloroethane

Условия реакции

Обработка

1. 1
   ДругоеThe organic material was separated
2. 2
   Экстракцияthe aqueous portion was extracted with dichloromethane (3×5 ml)
3. 3
   Сушкаdried (MgSO4)
4. 4
   Концентрированиеthen concentrated under reduced pressure
5. 5
   ДругоеThe residue was purified by flash chromatography (SiO2, gradient elution hexane to 3:1 hexane/ethyl acetate) which

Методика

Part C: Ethyl 3-(2-hydroxyphenyl)benzyloxyacetate (0.85 g, 2.97 mmol) was dissolved in 1,2-dichloroethane (25 ml) in a dry 50 ml flask. L-Fucose tetraacetate (1.97 g, 5.94 mmol) was added in one portion, then boron trifluoride etherate (1.86 ml, 14.84 mmol) was added slowly. The mixture was stirred under nitrogen overnight at room temperature then mixed with water (50 ml). The organic material was separated and the aqueous portion was extracted with dichloromethane (3×5 ml). The extracts were combined with the original organic fraction, dried (MgSO4) then concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, gradient elution hexane to 3:1 hexane/ethyl acetate) which provided 1.0 g (61%) of ethyl 3-(2-(2,3,4-tri-O acetyl-α-L-fucopyranosyloxy)phenyl)benzyloxyacetate.

Источник