تفاعل #215750

معادلة التفاعل

6-chloro-purine

triphenylphosphine

diethyl azodicarboxylate

3,5-bis(t-butyldimethylsiloxy)-1-hydroxy-2-desoxy-2,2-difluororibose

3,5-bis(t-butyldimethylsiloxy)-1-hydroxy-2-desoxy-2,2-difluororibose

→

1-(6-chloro-9H-purin-9-yl)-3,5-bis(t-butyldimethylsiloxy)-2-desoxy-2,2-difluororibose

المردود 34.3%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was stirred for an additional 6 hours at room temperature
2. 2
   أخرىThe solvent was evaporated under vacuum
3. 3
   workup.STIRRINGthe residue was stirred in a small amount of diethyl ether overnight
4. 4
   أخرىThe precipitated solid was removed by vacuum filtration
5. 5
   تركيزthe filtrate was concentrated under vacuum to dryness
6. 6
   أخرىThe residue was chromatographed over 70 g of silica
7. 7
   غسيلeluted with chloroform
8. 8
   workup.ADDITIONFractions containing the major component
9. 9
   أخرىthe solvent was evaporated

الإجراء التجريبي

To a solution of 0.77 g (5.0 mmol) of 6-chloro-purine in 50 ml of tetrahydrofuran was added 1.31 g (5.0 mmol) of triphenylphosphine and 0.87 g (5.0 mmol) of diethyl azodicarboxylate. To this solution was added a solution of 1.99 g (5.0 mmol) of 3,5-bis(t-butyldimethylsiloxy)-1-hydroxy-2-desoxy-2,2-difluororibose in tetrahydrofuran. The reaction mixture was stirred at room temperature for approximately 60 hours and an additional 0.66 g (1.7 mmol) of 3,5-bis(t-butyldimethylsiloxy)-1-hydroxy-2-desoxy-2,2-difluororibose was added to the reaction mixture. The mixture was stirred for an additional 6 hours at room temperature. The solvent was evaporated under vacuum and the residue was stirred in a small amount of diethyl ether overnight. The precipitated solid was removed by vacuum filtration and the filtrate was concentrated under vacuum to dryness. The residue was chromatographed over 70 g of silica and eluted with chloroform. Fractions containing the major component were combined and the solvent was evaporated therefrom to provide 1.0 g of 1-(6-chloro-9H-purin-9-yl)-3,5-bis(t-butyldimethylsiloxy)-2-desoxy-2,2-difluororibose. The structure of the product was verified by NMR. Mass spec.=477 [534-(t-butyl)]

المصدر