N,N-二异丙基乙胺 → 6-N-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)adenosine

HRID 1694677

反应方程式

HRID 1694677 反应方程式
[C:1]([NH:4][C:5]1[C:6]2[N:7]=[CH:8][N:9]([C:42]=2[N:43]=[CH:44][N:45]=1)[C@@H:10]1[O:41][C@H:15]([CH2:16][O:17][C:18]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C@@H:13]([OH:14])[C@H:11]1[OH:12])(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[C:55]([CH2:57][CH2:58][O:59][CH2:60]Cl)#[N:56].C(=O)(O)[O-].[Na+]>ClCCCl>[C:1]([NH:4][C:5]1[C:6]2[N:7]=[CH:8][N:9]([C:42]=2[N:43]=[CH:44][N:45]=1)[C@@H:10]1[O:41][C@H:15]([CH2:16][O:17][C:18]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C@@H:13]([OH:14])[C@H:11]1[O:12][CH2:60][O:59][CH2:58][CH2:57][C:55]#[N:56])(=[O:3])[CH3:2]

参与物

6

反应物 4

HCID 81531N,N-二异丙基乙胺HCID 516892碳酸氢钠HCID 116654052-Cyanoethyl chloromethyl etherHCID 71356814英文名称:N6-ACETYL-5'-O-(4,4'-DIMETHOXYTRITYL)ADENOSINE

产物 1

HCID 866307246-N-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)adenosine收率 33%

试剂、催化剂与溶剂 1

HCID 111,2-二氯乙烷溶剂

反应条件

温度
80 °C

实验过程

N6-Acetyl-5′-O-(4,4′-dimethoxytrityl)adenosine (22.0 g, 36.0 mmol) was dissolved in 170 mL of 1,2-dichloroethane, and 16.3 g of diisopropylethylamine (126 mmol) was added, and 12.1 g of dibutylstannyl dichloride (39.7 mmol) was added subsequently. Then, the reaction was performed at room temperature for 1 hour. Then, the reaction solution was heated up to 80° C., and 4.30 g of chloromethyl 2-cyanoethyl ether (36.0 mmol) was added dropwise, and the solution was stirred for 30 minutes. After the reaction completed, the reaction solution was added to an aqueous saturated sodium bicarbonate solution, and was subjected to extraction with methylene chloride. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The obtained mixture was purified by silica gel column chromatography to obtain N6-acetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl) adenosine (7.47 g, yield 33%).

后处理

  1. extractionwas subjected to extraction with methylene chloride
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe obtained mixture was purified by silica gel column chromatography

来源与证据

ORD记录
ord-41417203306d4df692589c32184f1708
来源数据集
uspto-grants-2012_04
专利号
US08158775B2

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