Reaktion #51520

Reaktionsgleichung

benzoyl chloride

Trimethylchlorosilane

benzoyl chloride

NH4OH

3′-O-allyl adenosine

P2O5

→

title compound

Ausbeute 62.0%

3′-O-allyl-N6-benzoyl adenosine

Ausbeute 62.0%

Lösungsmittel

pyridine

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas brought to room temperature
2. 2
   workup.STIRRINGstirred for 4 hrs
3. 3
   SonstigeThen 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
   Sonstigeat 0° C.
6. 6
   workup.STIRRINGstirring for an additional 1 hr
7. 7
   SonstigeSolvent evaporated residue
8. 8
   Sonstigepartitioned between water and ether
9. 9
   SonstigeProduct precipitates as an oil, which
10. 10
    Sonstigewas then chromatographed (5% MeOH in CH2Cl2)

Vorschrift

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%).

Quelle