تفاعل #2146749

معادلة التفاعل

1,3,5-tri-O-benzoyl-α-D-ribofuranose

Trichloroisocyanuric acid

TEMPO

→

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

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled under ice
2. 2
   أخرىThe ice bath is removed
3. 3
   ترشيحthen filtered on Celite®
4. 4
   غسيلThe organic phase is washed with saturated aqueous Na2CO3 solution
5. 5
   تجفيفThe organic layer is dried (MgSO4)
6. 6
   أخرىthe solvent is evaporated

الإجراء التجريبي

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).

المصدر