反応 #2146749

反応方程式

1,3,5-tri-O-benzoyl-α-D-ribofuranose

Trichloroisocyanuric acid

TEMPO

→

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

溶媒

dichloromethane

反応条件

後処理

1. 1
   温度cooled under ice
2. 2
   その他The ice bath is removed
3. 3
   ろ過then filtered on Celite®
4. 4
   洗浄The organic phase is washed with saturated aqueous Na2CO3 solution
5. 5
   乾燥The organic layer is dried (MgSO4)
6. 6
   その他the solvent is evaporated

実験手順

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).

出典