Reacción #159786

Ecuación de reacción

6-[2-bromo-5-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-2-yl)-benzyl]-chroman

triethylsilane

boron trifluoride

→

6-[2-bromo-5-((3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzyl]-chroman

Rendimiento 69.2%

Disolventes

acetonitrile dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat 0° C
2. 2
   Otrothe reaction was quenched with saturated aqueous sodium bicarbonate solution
3. 3
   OtroThe volatiles were evaporated under reduced pressure
4. 4
   Extracciónthe resulting mixture was extracted with ethyl acetate (2×10 mL)
5. 5
   Secadodried over sodium sulfate
6. 6
   Concentraciónthen concentrated to a residue which
7. 7
   Otrowas purified by silica gel column chromatography

Procedimiento

To a stirred solution of 6-[2-bromo-5-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-2-yl)-benzyl]-chroman (900 mg, 1.05 mmol) in acetonitrile: dichloromethane (1:1 mixture, 6 mL) was added triethylsilane (0.34 mL, 2.1 mmol) and boron trifluoride diethyletharate complex (0.19 mL, 1.58 mmol), at 0° C. After stirring for 2 h, the reaction was quenched with saturated aqueous sodium bicarbonate solution. The volatiles were evaporated under reduced pressure; the resulting mixture was extracted with ethyl acetate (2×10 mL). The organic layers were combined and dried over sodium sulfate then concentrated to a residue which was purified by silica gel column chromatography to furnish 6-[2-bromo-5-((3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzyl]-chroman (600 mg).

Fuente