Реакция #51520

Уравнение реакции

benzoyl chloride

Trimethylchlorosilane

benzoyl chloride

NH4OH

3′-O-allyl adenosine

P2O5

→

title compound

Выход 62.0%

3′-O-allyl-N6-benzoyl adenosine

Выход 62.0%

Растворители

pyridine

Water

Условия реакции

Обработка

1. 1
   Другоеwas brought to room temperature
2. 2
   workup.STIRRINGstirred for 4 hrs
3. 3
   ДругоеThen 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
   Другоеat 0° C.
6. 6
   workup.STIRRINGstirring for an additional 1 hr
7. 7
   ДругоеSolvent evaporated residue
8. 8
   Другоеpartitioned between water and ether
9. 9
   ДругоеProduct precipitates as an oil, which
10. 10
    Другоеwas then chromatographed (5% MeOH in CH2Cl2)

Методика

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%).

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