Deoxyuridine → 3',5'-o-Bis-tert-butyldimethylsilyl-2'-deoxyuridine

HRID 600113

反応式

HRID 600113 の反応式
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Si:21]([C@@:3]1([OH:4])[C@@H:5]([CH2:6][O:7][Si:21]([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22])[O:8][C@@H:1]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:2]1)([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]

参加物

4

反応物 2

HCID 13712DeoxyuridineHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 1317287273',5'-o-Bis-tert-butyldimethylsilyl-2'-deoxyuridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Under a nitrogen atmosphere, a mixture of 2′-deoxyuridine dU (2.5 g, 10.95 mmol), TBSCl (7.26 g, 48.2 mmol) and imidiazole (6.56 g, 96.4 mmol) in anhydrous DMF (25 mL) was stirred at 0° C. for two hours and then warmed to room temperature over one hour. The reaction mixture was concentrated in vacuo and purified by silica gel column chromatography to yield 3′,5′-O-bis-tert-butyldimethylsilyl-2′-deoxyuridine dC.11 (4.62 g, 92%) as a white foam.

後処理

  1. temperaturewarmed to room temperature over one hour
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-1737065a908c4e5d8435e94f91347f74
出典データセット
uspto-grants-2011_03
特許番号
US07897737B2

関連ノート

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