Reacción #51520

Ecuación de reacción

benzoyl chloride

Trimethylchlorosilane

benzoyl chloride

NH4OH

3′-O-allyl adenosine

P2O5

→

title compound

Rendimiento 62.0%

3′-O-allyl-N6-benzoyl adenosine

Rendimiento 62.0%

Disolventes

pyridine

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas brought to room temperature
2. 2
   workup.STIRRINGstirred for 4 hrs
3. 3
   OtroThen the reaction mixture was brought to 0° C. in an ice bath
4. 4
   workup.STIRRINGthe reaction mixture was stirred for 30 minutes
5. 5
   Otroat 0° C.
6. 6
   workup.STIRRINGstirring for an additional 1 hr
7. 7
   OtroSolvent evaporated residue
8. 8
   Otropartitioned between water and ether
9. 9
   OtroProduct precipitates as an oil, which
10. 10
    Otrowas then chromatographed (5% MeOH in CH2Cl2)

Procedimiento

2′/3′-O-allyl adenosine (15.19 g, 51.1 mmol) was dried over P2O5 under high vacuum overnight at 40° C. It was then dissolved in anhydrous pyridine (504.6 mL) under inert atmosphere. Trimethylchlorosilane (32.02 mL, 252.3 mmol) was added at 0° C. and the reaction mixture was stirred for 1 hr under inert atmosphere. Then benzoyl chloride (29.4 mL, 252.3 mmol) was added dropwise. Once the addition of benzoyl chloride was over, the reaction mixture was brought to room temperature and stirred for 4 hrs. Then the reaction mixture was brought to 0° C. in an ice bath. Water (100.9 mL) was added and the reaction mixture was stirred for 30 minutes. Then NH4OH (100.0 mL, 30% aqueous solution w/w) was added, keeping the reaction mixture at 0° C. and stirring for an additional 1 hr. Solvent evaporated residue partitioned between water and ether. Product precipitates as an oil, which was then chromatographed (5% MeOH in CH2Cl2) to get the title compound as a white foam (12.67 g, 62%).

Fuente