Reacción #2146749

Ecuación de reacción

1,3,5-tri-O-benzoyl-α-D-ribofuranose

Trichloroisocyanuric acid

TEMPO

→

(2R,4R,5R)-2,4-dibenzoyloxy-5-benzoyloxymethyl-dihydrofuran-3-one

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled under ice
2. 2
   OtroThe ice bath is removed
3. 3
   Filtraciónthen filtered on Celite®
4. 4
   LavadoThe organic phase is washed with saturated aqueous Na2CO3 solution
5. 5
   SecadoThe organic layer is dried (MgSO4)
6. 6
   Otrothe solvent is evaporated

Procedimiento

1,3,5-tri-O-benzoyl-α-D-ribofuranose (10.0 g, 21.62 mmol, 1.0 equiv.) is dissolved in dichloromethane (60 ml) and cooled under ice. Trichloroisocyanuric acid (5.52 g, 23.80 mmol, 1.1 equiv.) is added, followed by addition of catalytic amount of TEMPO. The ice bath is removed and the mixture is stirred at room temperature for 1 hour then filtered on Celite®. The organic phase is washed with saturated aqueous Na2CO3 solution, followed by 1N HCl and brine. The organic layer is dried (MgSO4) and the solvent is evaporated to give (2R,4R,5R)-2,4-dibenzoyloxy-5-benzoyloxymethyl-dihydrofuran-3-one as a white foam. 1H-NMR (400 MHz, CDCl3): δ 8.13-8.01 (m, 6H), 7.65-7.37 (m, 9H), 6.20 (d, 1H, J=1.2 Hz), 5.88 (dd, 1H, J=1.2 Hz, 8.8 Hz), 5.05 (m, 1H, J=1.2 Hz, 4 Hz, 8.8 Hz), 4.84 (dd, 1H, J=4 Hz, 12.4 Hz), 4.65 (dd, 1H, J=4 Hz, 12.4 Hz).

Fuente