Tetrabutylammonium Fluoride → HCID 86746616, compound

HRID 1613142Notes

Reaction equation

HRID 1613142 reaction equation
[C:1]([C@@:9]1([N:26]2[CH:34]=[C:32]([CH3:33])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[O:23][C:20]([CH2:24][OH:25])([CH2:21][OH:22])[C@@H:11]([O:12][Si](C(C)(C)C)(C)C)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([C@@:9]1([N:26]2[CH:34]=[C:32]([CH3:33])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[O:23][C:20]([CH2:24][OH:25])([CH2:21][OH:22])[C@@H:11]([OH:12])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131717801HCID 131717801, compound

Product 1

HCID 86746616HCID 86746616, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N3 -benzoyl-3'-O-t-butyldimethylsilyl-4'-hydroxymethyl thymidine (0.5 g, 1.02 mM) in THF (3 ml) was treated with tetrabutylammonium fluoride in THF (1 M, 1.5 ml, 1.5 mM) at 24° C. for 4 hours. The solvent was removed and the residue was chromatographed on silica gel with 7% CH3OH/CH2Cl2 to give N3 -benzoyl-4'-hydroxymethyl thymidine (0.3 g, 0.83 mM).

Workup

  1. customThe solvent was removed
  2. customthe residue was chromatographed on silica gel with 7% CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-4536a84cde7b45e7ace50ce395d873f0
Source dataset
uspto-grants-1993_03
Patent number
US05192749

Reaction notes

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