Methanol → 5'-O-tert-butyldiphenylsilyl-N6-benzoyl-2'-O-(2,3-dihydroxypropyl)-adenosine

Participants

Reaction Steps

Compound 111 (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 112 (5.9 g) and used for next step without purification. Rf 0.17 (5% MeOH in CH2Cl2)

Provenance & Evidence