Реакция #2146752

Уравнение реакции

(2R,3R,4R,5R)-2,4-dibenzoyloxy-5-benzoyloxymethyl-3-ethynyl-tetrahydro-furan-3-ol

K2CO3

→

(2R,3R,4R,5R)-4-benzoyloxy-5-benzoyloxymethyl-3-ethynyl-tetrahydrofuran-2,3-diol

Растворители

THF

methanol

Условия реакции

Обработка

1. 1
   Фильтрацияfiltered on silica gel
2. 2
   Концентрированиеconcentrated
3. 3
   Другоеpurified by flash chromatography

Методика

Intermediate (2R,3R,4R,5R)-2,4-dibenzoyloxy-5-benzoyloxymethyl-3-ethynyl-tetrahydro-furan-3-ol (2.048 g, 4.21 mmol, 1.0 equiv.) is dissolved in methanol (10 ml) and THF (10 ml). K2CO3 (176 mg, 1.26 mmol, 0.3 equiv.) is added, The reaction is stirred at ambient temperature for 2 h, filtered on silica gel, concentrated and purified by flash chromatography to give (2R,3R,4R,5R)-4-benzoyloxy-5-benzoyloxymethyl-3-ethynyl-tetrahydrofuran-2,3-diol as a foam. 1H-NMR (400 MHz, CDCl3): δ 8.06-7.96 (m, 4H), 7.54-7.26 (m, 6H), 5.88 (d, 0.26H, J=6.4 Hz), 5.54 (s, 0.72H), 5.53 (d, 0.72H, J=5.2 Hz), 5.41 (s, 0.28H), 5.28 (bs, 1H), 4.67-4.49 (m, 3H), 4.22 (bs, 1H), 2.67 (s, 0.26H), 2.59 (s, 0.71H); 13C-NMR (100 MHz, CDCl3): δ 166.74, 166.61, 165.74, 165.66, 133.79, 133.71, 133.52, 133.33, 133.24, 130.11, 130.05, 130.02, 129.89, 129.81, 129.44, 129.41, 128.86, 128.75, 128.57, 128.41, 128.36, 81.87, 80.07, 79.23, 77.89, 77.21, 76.61, 76.39, 75.77, 75.58, 72.83, 65.29, 64.26.

Источник