反应 #1365737

反应方程式

Compound 5

6-N-(4-Monomethoxytrityl)-9-(3,5-di-O-benzoyl-2-deoxy-β-L-threo-pentofuranosyl)adenine

→

6

收率 98.4%

6-N-(4-Monomethoxytrityl)-9-(2-deoxy-β-L-threo-pentofuranosyl)-adenine

收率 98.4%

溶剂

ammonia

反应条件

后处理

1. 1
   浓缩After concentration
2. 2
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane (60 mL)
3. 3
   洗涤washed with water (30 mL)
4. 4
   萃取The aqueous layer was extracted twice with dichloromethane (10 mL)
5. 5
   其他The combined organic layer was dried
6. 6
   过滤filtered
7. 7
   浓缩concentrated
8. 8
   其他The residue was purified by silica gel column chromatography (0-5% MeOH in dichloromethane)

实验过程

Compound 5 (0.95 g, 1.30 mmol) was treated with a solution (saturated at −10° C.) of methanolic ammonia (40 mL), at room temperature overnight. After concentration, the residue was dissolved in dichloromethane (60 mL) and washed with water (30 mL). The aqueous layer was extracted twice with dichloromethane (10 mL). The combined organic layer was dried, filtered and concentrated. The residue was purified by silica gel column chromatography (0-5% MeOH in dichloromethane) to give pure 6 (0.67 g, 98%) as a foam: 1H NMR (CDCl3): δ2.6-2.9 (m, 2H, H-2′and H-2″), 3.5 (br s, 1H, OH-5′), 3.55 (s, 3H, OCH3), 3.9-4.0 (m, 3H, H-4′, H-5′ and H-5″), 4.5-4.6 (m, 1H, H-3′), 6.03 (dd, 1H, H-1′, J1′,2′=4.0 Hz, J1′,2″=8.8 Hz), 7.0 (br s, 1H, NH-6), 6.7-6.8 and 7.1-7.4 (2m, 14H, MMTr), 7.40 (d, 1H, OH-3′JH,OH=10.6 Hz), 7.80 and 7.99 (2s, 2H, H-2 and H-8); ms: matrix G/T, (FAB+) m/z 524 [M+H]+, 408 [BH2]+, (FAB−) m/z 1045 [2M−H]−, 522 [M−H]−, 406 [B]−; UV (95% ethanol): λmax 275 nm (ε 12300), λmin 247 nm (ε3600); [α]D20=+28 (c 0.94, DMSO).

来源