Reacción #6875

Ecuación de reacción

4,4′-dimethoxytrityl chloride

nucleoside

1-(3-O-Benzyl-4-C-(p-Toluenesulphonyloxymethyl)β-D-xylofuranosyl)thymine

4,4′-dimethoxytrityl chloride

→

nucleoside

Rendimiento 75.0%

1-(3-O-Benzyl-5-O-(4,4′-dimethoxytrityl)-4-C-(p-toluenesulphonyloxymethyl)-β-D-xylofuranosyl)thymine

Rendimiento 75.0%

Disolventes

dichloromethane

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 36 h at room temperature
3. 3
   OtroThe organic phase was separated
4. 4
   Lavadowashed with saturated aqueous solutions of sodium hydrogen carbonate (25 cm3×3) and brine (40 cm3×3)
5. 5
   Secadodried (Na2SO4)
6. 6
   Otroevaporated to dryness under reduced pressure
7. 7
   OtroThe residue was purified by silica gel column chromatography

Procedimiento

To a solution of nucleoside 6 (3.66 g, 6.88 mmol) in anhydrous pyridine (25 cm3) was added N,N-(dimethylamino)pyridine (0.84 g, 6.81 mmol) and 4,4′-dimethoxytrityl chloride (3.5 g, 13.2 mmol) and the mixture was stirred for 23 h at room temperature. Additional N,N-(dimethylamino)pyridine (0.250 g, 2.06 mmol) and 4,4′-dimethoxytrityl chloride (0.700 g, 2.06 mmol) was added, and stirring was continued for 36 h at room temperature. Ice cold H2O (50 cm3) was added and the reaction mixture was diluted with dichloromethane (150 cm3). The organic phase was separated and washed with saturated aqueous solutions of sodium hydrogen carbonate (25 cm3×3) and brine (40 cm3×3), dried (Na2SO4) and evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol/pyridine (0.75–1.5% methanol; 0.5% pyridine, v/v/v) as eluent to afford nucleoside 7 (4.28 g, 75%) as a white solid material after evaporation of the solvents under reduced pressure.

Fuente