تفاعل #417915
ord-c8a0439acf424376a93f954532d0131b
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1أخرىquenched with 100 mL saturated NaHCO3 solution
- 2استخلاصAfter the aqueous layer was extracted with dichloromethane (100 mL) three times
- 3أخرىevaporated
- 4أخرىThe residue was purified by flash chromatography (gradient
الإجراء التجريبي
Under the protection of N2, to a solution of 9-(2-O-benzyl-β-D-arabinofuranosyl)-6-[2-(trimethylsilyl)ethoxy]-9H-purine (1.60 g, 3.49 mmol) in 20 mL pyridine was added 4,4′-dimethoxytrityl chloride (2.13 g, 6.28 mmol). The mixture was stirred at room temperature for 2 h. The reaction was diluted with 100 mL dichloromethane and quenched with 100 mL saturated NaHCO3 solution. After the aqueous layer was extracted with dichloromethane (100 mL) three times, the organic layers were combined and evaporated. The residue was purified by flash chromatography (gradient: hexane with EtOAc 0-100%, with 1% triethylamine in both hexane and EtOAc) to produce 1.18 g (1.55 mmol, 44.4%) product. LCMS: for C43H48N4O7Si calculated 760.9. found 762.5 [M+H]+. 1H NMR (600 MHz, CD3CN) δ: 8.39 (s, 1H), 8.10 (s, 1H), 7.42-7.40 (m, 2H), 7.29-7.13 (m, 10H), 6.86-6.85 (m, 2H), 6.81-6.77 (m, 4H), 6.50 (d, J=5.5 Hz, 1H), 4.69-4.65 (m, 2H), 4.49-4.45 (m, 2H), 4.24-4.21 (m, 2H), 4.02 (m, 1H), 3.8 (dd, 10.4, 6.3 Hz, 1H), 3.29 (dd, J=10.4, 3.5 Hz, 1H), 1.22 (m, 2H), 0.09 (s, 1H). 13C NMR (600 MHz, CD3CN) δ: 160.82, 152.01, 142.44, 130.24, 130.21, 128.39, 128.25, 128.01, 127.86, 127.61, 127.05, 113.21, 83.56, 82.87, 82.37, 74.31, 72.54, 65.26, 63.56, 55.10, 17.27, −2.13.