Imidazole → 3'-O-(t-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)thymidine

HRID 378540

反応式

HRID 378540 の反応式
[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([C:7]([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]3=[O:31])[CH2:26][C@@H:25]2[OH:38])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.N1C=CN=C1.[Si:46](Cl)([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([C:7]([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]3=[O:31])[CH2:26][C@@H:25]2[O:38][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1624195'-O-(4,4'-Dimethoxytrityl)thymidine

生成物 1

HCID 108760643'-O-(t-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)thymidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 13.0 g (23.9 mmol) 5'--O--(4,4'-dimethoxytrityl)thymidine 16 in 50 ml DMF was added 3.0 g (44 mmol) imidazole and 3.6 g (23.9 mmol) tert-butyl-dimethylsilyl chloride. The solution was stirred at room temperature for 3 hours. DMF was then removed in vacuo and the residue was dissolved in 300 ml of ethyl acetate. The solution was washed with water and the organic layer was dried over MgSO4. After concentration of the solution and recrystallization from ethyl acetate/hexane, the solid product 5'--O--(4,4'-dimethoxy)-3'-(tert-butyldimethylsilyl)thymidine 17 was used directly for the next reaction.

後処理

  1. customDMF was then removed in vacuo
  2. dissolutionthe residue was dissolved in 300 ml of ethyl acetate
  3. washThe solution was washed with water
  4. dry with materialthe organic layer was dried over MgSO4
  5. customAfter concentration of the solution and recrystallization from ethyl acetate/hexane
  6. customthe solid product 5'--O--(4,4'-dimethoxy)-3'-(tert-butyldimethylsilyl)thymidine 17 was used directly for the next reaction

出典と根拠

ORDレコード
ord-6a1c62e3863f457288286234120e4eb8
出典データセット
uspto-grants-2000_02
特許番号
US06031092

関連ノート

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