반응 #2146749

반응 방정식

1,3,5-tri-O-benzoyl-α-D-ribofuranose

Trichloroisocyanuric acid

TEMPO

→

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

용매

dichloromethane

반응 조건

후처리

1. 1
   온도cooled under ice
2. 2
   기타The ice bath is removed
3. 3
   여과then filtered on Celite®
4. 4
   세척The organic phase is washed with saturated aqueous Na2CO3 solution
5. 5
   건조The organic layer is dried (MgSO4)
6. 6
   기타the solvent is evaporated

실험 절차

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).

출처