反应 #1951036

反应方程式

2,5,6-Trichloro-3-acetyl-1-[3,5-di-O-(p-toluoyl)-2-deoxy-β-D-ribofuranosyl]indole

sodium methoxide

→

4.117

收率 74.0%

2,5,6-Trichloro-3-acetyl-1-(2-deoxy-β-D-ribofuranosyl)indole

收率 74.0%

溶剂

MeOH

反应条件

后处理

1. 1
   其他a precipitate then formed
2. 2
   workup.WAITto stand at 4° C. for 4 h
3. 3
   过滤was then filtered
4. 4
   洗涤the solids rinsed with cold MeOH (10 mL)
5. 5
   其他The solid was recrystallized
6. 6
   温度from warm MeOH

实验过程

2,5,6-Trichloro-3-acetyl-1-[3,5-di-O-(p-toluoyl)-2-deoxy-β-D-ribofuranosyl]indole (4.116, 0.62 g, 1.0 mmol) was suspended in dry MeOH (50 mL) to which was added sodium methoxide (220 mg, 4.1 mmol). The suspension was stirred at room temperature for 16 h, after which time the solution first clarified and a precipitate then formed. The suspension was allowed to stand at 4° C. for 4 h, and was then filtered, and the solids rinsed with cold MeOH (10 mL). The solid was recrystallized from warm MeOH to yield 0.28 g (74%) of 4.117 as a white crystalline solid: mp dec. >200 C; Rf0.4 (10% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 8.52 (s, 1H), 8.37 (s, 1H), 6.49 (dd, 1H), 5.43 (s, 1H, D2O exch.), 5.26 (s, 1H, D2O exch.), 4.45 (m, 1H), 3.89 (d, 1H), 3.72 (m, 2H), 2.60 (s, 3H), 2.49 (m, 1H), 2.13 (m, 1H). 13C-NMR (125 MHz, DMSO-d6): δ 192.13, 132.15, 131.99, 126.12, 125.50, 125.65, 121.96, 115.25, 112.85, 87.55, 85.43, 69.81, 60.67, 47.10, 30.68. HRMS (EI) m/z calcd. for C15H14Cl3NO4 376.9988, found 376.9982. Anal calcd for C15H14Cl3NO4: C, 47.58; H, 3.73; N, 3.70. Found: C, 47.52; H, 3.95; N, 3.59.

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