Реакция #417911

Уравнение реакции

1,4-anhydro-2-O-benzyl-D-ribitol

pyridine

4,4′-dimethoxytrityl chloride

→

pure product

Выход 70.2%

1,4-Anhydro-2-O-benzyl-5-O-[bis(4-methoxyphenyl)(phenyl)methyl]D-ribitol

Выход 70.2%

Условия реакции

Обработка

1. 1
   ДругоеSolvent was then evaporated in vacuo
2. 2
   Другоеthe residue purified by flash chromatography

Методика

To a solution of 1,4-anhydro-2-O-benzyl-D-ribitol (1.0 g, 4.46 mmol) in pyridine (20 mL, 247 mmol) was added 4,4′-dimethoxytrityl chloride (4.53 g, 13.38 mmol). The mixture was stirred at ambient temperature for 2 h. Solvent was then evaporated in vacuo, and the residue purified by flash chromatography using 25-30% ethyl acetate in hexane to obtain 1.65 g (3.13 mmol, 70%) of the pure product. LCMS: for C33H34O6 calculated 526.2. found 549.2 [M+H]+. 1H NMR (600 MHz, CD3CN) δ: 7.42, (m, 2H), 7.37 (m, 4H), 7.30 (m, 7H), 7.21 (tt, J=7.3, 1.1 Hz, 1H), 6.85 (m, 4H), 4.61 (d, J=3.4 Hz, 2H), 4.05 (dd, J=9.9, 4.7 Hz, 1H), 4.01 (m, 2H), 3.81 (m, 2H), 3.76 (s, 2H), 3.76 (s, 6H), 3.17 (dd, J=10.2, 3.2 Hz, 1H), 3.00 (dd, J=10.2, 5.0, 1H), 2.97 (s, 1H). 13C NMR (600 MHz, CD3CN) δ: 158.84, 130.21, 128.59, 128.27, 128.01, 127.88, 126.98, 117.53, 113.22, 82.73, 78.59, 72.28, 71.87, 70.21, 64.44, 55.11.

Источник