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
Reaction equation
[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]Participants
4
Procedure
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.
Workup
- concentrationThe mixture was then concentrated in vacuo
- dissolutiondissolved in CH2Cl2 (100 mL)
- washwashed twice with water (50 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- custompurified by silica gel chromatography
Sources & evidence
- ORD record
- ord-84ad6101302d452794849dc43974e84d
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198029B2
Reaction notes
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