反応 #51522

反応方程式

Ethyl acetate

3′-O-allyl-5′-O-tert-butyldiphenylsilyl-N6-benzoyl-adenosine

4-methylmorpholine N-oxide

dioxane

MeOH

→

title compound

5′-O-tert-butyldiphenylsilyl-N6-benzoyl-2′-O-(2,3-dihydroxypropyl)-adenosine

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他Reaction
2. 2
   その他the resulting reaction mixture
3. 3
   洗浄was washed with water (1×50 mL)
4. 4
   乾燥Ethyl acetate layer was dried over anhydrous Na2SO4
5. 5
   その他evaporated

実験手順

3′-O-allyl-5′-O-tert-butyldiphenylsilyl-N6-benzoyl-adenosine (5.5 g, 8.46 mmol), 4-methylmorpholine N-oxide (1.43 g, 12.18 mmol) were dissolved in dioxane (45.42 mL). 4% aqueous solution of OSO4 (1.99 mL, 0.31 mmol) was added. The reaction mixture was protected from light and stirred for 3 hrs. Reaction was monitored by TLC (5% MeOH in CH2Cl2). Ethyl acetate (100 mL) was added and the resulting reaction mixture was washed with water (1×50 mL). Ethyl acetate layer was dried over anhydrous Na2SO4 and evaporated to get the title compound (5.9 g) and used for next step without purification. Rf 0.17 (5% MeOH in CH2Cl2)

出典