tert-Butyldimethylsilyl chloride → HCID 137227856, compound

HRID 600115Notes

Reaction equation

HRID 600115 reaction equation
[C@@H:1]1([N:9]2[C:19]3[N:18]=[C:16]([NH2:17])[NH:15][C:13](=[O:14])[C:12]=3[N:11]=[CH:10]2)[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22]>CN(C=O)C>[Si:24]([C@@:3]1([OH:4])[C@@H:5]([CH2:6][O:7][Si:24]([C:21]([CH3:23])([CH3:22])[CH3:20])([CH3:26])[CH3:25])[O:8][C@@H:1]([N:9]2[C:19]3[N:18]=[C:16]([NH2:17])[NH:15][C:13](=[O:14])[C:12]=3[N:11]=[CH:10]2)[CH2:2]1)([C:21]([CH3:23])([CH3:22])[CH3:20])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 135398592Deoxyguanosine

Product 1

HCID 137227856HCID 137227856, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2′-deoxyguanosine dG (0.89 g, 3.30 mmol), imidiazole (2.0 g, 29.32 mmol), and TBSCl (2.34 g, 15.55 mmol) were added to anhydrous DMF (8 mL) at 0° C. under a N2 atmosphere. The reaction mixture was gradually warmed to room temperature and stirred overnight. The mixture was then concentrated in vacuo, treated with a mixture of CHCl3 (8 mL) and MeOH (8 mL), concentrated in vacuo, and purified by silica gel chromatography to yield 3′,5′-O-bis-tert-butyldimethylsilyl-2′-deoxyguanosine dG.01 (1.57 g, 96%) as a white powder.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. additiontreated with a mixture of CHCl3 (8 mL) and MeOH (8 mL)
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-5ad436e00ba94422a6e0109ba4f4d771
Source dataset
uspto-grants-2011_03
Patent number
US07897737B2

Reaction notes

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