تفاعل #6877

معادلة التفاعل

Nucleoside

(1R,3R,4R,7R)-7-Benzyloxy-1-(4,4′-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

→

nucleoside

المردود 82.0%

(1S,3R,4R,7R)-7-hydroxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo [2.2.1]heptane

المردود 82.0%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture was degassed
2. 2
   ترشيحthe mixture was filtered (silica gel
3. 3
   غسيلwashed with dichloromethane/methanol (700 cm3
4. 4
   تركيز1:3, v/v)) and the volume of the filtrate was concentrated to 25% of its initial volume
5. 5
   ترشيحfiltration
6. 6
   أخرىthe filtrate was evaporated to dryness under reduced pressure

الإجراء التجريبي

Nucleoside 8 (3.09 g, 4.66 mmol) was dissolved in methanol (40 cm3) and 10% palladium on carbon (3 g, suspended in methanol (20 cm3)) was added. The mixture was degassed and stirred under an atmosphere of hydrogen. After 26 h, the mixture was filtered (silica gel, washed with dichloromethane/methanol (700 cm3; 1:3, v/v)) and the volume of the filtrate was concentrated to 25% of its initial volume. After repeated filtration, the filtrate was evaporated to dryness under reduced pressure and the residue was subjected to column chromatography on silica gel using dichloromethane/methanol (5–12% methanol, v/v) as eluent furnishing nucleoside 9 (1.03 g, 82%) as a white solid material after evaporation of the solvents under reduced pressure.

المصدر