반응 #6875

반응 방정식

4,4′-dimethoxytrityl chloride

nucleoside

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

4,4′-dimethoxytrityl chloride

→

nucleoside

수율 75.0%

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

수율 75.0%

용매

dichloromethane

pyridine

반응 조건

후처리

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

실험 절차

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.

출처