تفاعل #82472

معادلة التفاعل

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

المردود 61.0%

المذيبات

1,2-dichloroethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر