Reaktion #2146749

Reaktionsgleichung

1,3,5-tri-O-benzoyl-α-D-ribofuranose

Trichloroisocyanuric acid

TEMPO

→

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

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled under ice
2. 2
   SonstigeThe ice bath is removed
3. 3
   Filtrationthen filtered on Celite®
4. 4
   WaschenThe organic phase is washed with saturated aqueous Na2CO3 solution
5. 5
   TrocknenThe organic layer is dried (MgSO4)
6. 6
   Sonstigethe solvent is evaporated

Vorschrift

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).

Quelle