tert-Butyldimethylsilyl chloride → 9-[(2R,4R,5R)-4-[tert-butyl(dimethyl)silyl]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-3H-purin-6-one

HRID 217571

反応式

HRID 217571 の反応式
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].[C@@H:9]1([N:17]2[C:26]3[N:25]=[CH:24][N:23]=[C:21]([OH:22])[C:20]=3[N:19]=[CH:18]2)[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[CH2:10]1>CN(C=O)C>[Si:5]([C@@:11]1([OH:12])[C@@H:13]([CH2:14][O:15][Si:5]([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6])[O:16][C@@H:9]([N:17]2[C:26]3[N:25]=[CH:24][N:23]=[C:21]([OH:22])[C:20]=3[N:19]=[CH:18]2)[CH2:10]1)([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

参加物

4

反応物 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 178521064HCID 178521064、化合物

生成物 1

HCID 1784552339-[(2R,4R,5R)-4-[tert-butyl(dimethyl)silyl]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-3H-purin-6-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of TBSCl (1.91 g, 12.67 mmol) was added to a solution of 2′-deoxyinosine (1.00 g, 3.96 mmol) and imidiazole (1.73 g, 25.34 mmol) in anhydrous DMF (3 mL) at 0° C. under nitrogen atmosphere. The reaction mixture was gradually warmed to room temperature and stirred for 12 hours. The mixture was then concentrated in vacuo, dissolved in CH2Cl2 (100 mL), washed twice with water (50 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 3′,5′-O-bis-tert-butyldimethylsilyl-2′-deoxyinosine dA.n9 (1.58 g, 83%) as a white powder.

後処理

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutiondissolved in CH2Cl2 (100 mL)
  3. washwashed twice with water (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-84ad6101302d452794849dc43974e84d
出典データセット
uspto-grants-2012_06
特許番号
US08198029B2

関連ノート

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