Reacción #81751

Ecuación de reacción

N6 -methyladenosine

m-chloroperbenzoic acid

Water

→

N6 -Methyladenosine N1 -oxide

Rendimiento 45.0%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroa resulting thick precipitate was removed by filtration
2. 2
   Otrothe foamy residue was chromatographed on a silica gel column (CHCl3 : MeOH 2:1)
3. 3
   OtroThe product was obtained as a white solid (mp 145° C., crystallization from EtOH) in 45% yield (0.9 g)

Procedimiento

A solution of N6 -methyladenosine (2 g, 6.7 mmol) and m-chloroperbenzoic acid (2.3 g, 13.4 mmol) in acetic acid (20 ml) was stirred at room temperature for two days. Water (20 ml) was added to the reaction mixture, and a resulting thick precipitate was removed by filtration and discarded. The filtrate was co-evaporated repeatedly with water under high vacuum, and the foamy residue was chromatographed on a silica gel column (CHCl3 : MeOH 2:1). The product was obtained as a white solid (mp 145° C., crystallization from EtOH) in 45% yield (0.9 g). 1H NMR (DMSO)d: 8.62 (s, H-2), 8.55 (s, H-8), 5.88 (d, J=5.4 Hz, 1H, H-1), 4.51 (`t`, J=5.1 Hz, 1H, H-2'), 4.15 (`t`, J=4.5 Hz, 1H, H-3'), 3.94 (ABq, 1H, H-4'), 3.61 (ABdq, J=12, 4 Hz, 2H, H-5'), 3.46 (s, 3H, Me) ppm. MS (CI) m/e: 298 (MH+).

Fuente