Novel epimerization of aromatic C-nucleosides with electron-withdrawing substituents with trifluoroacetic acid-benzenesulfonic acid using mild conditions

Tetrahedron Letters

Volumn 44, Issue 21, 2003, Pages 4051-4055

  Jiang, Yu Lin ^a   Stivers, James T ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Benzenesulfonic acid; C nucleosides; Dichloromethane; Epimerization; Trifluoroacetic acid

Indexed keywords

BENZENESULFONIC ACID DERIVATIVE; NUCLEOSIDE DERIVATIVE; TRIFLUOROACETIC ACID;

ARTICLE; CATALYST; COLUMN CHROMATOGRAPHY; DNA SYNTHESIS; DRUG SYNTHESIS; ELECTRON TRANSPORT; ENVIRONMENTAL TEMPERATURE; EPIMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLID;

EID: 0038218487     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00848-7     Document Type: Article

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16. Combination catalyst. Trifluoroacetic acid (0.50 ml, 0.74g, 6.4 mmol) was added to benzenesulfonic acid (0.22g, 1.4 mmol). The mixture was vortexed and centrifuged to give a clear solution (0.58 ml). The residue was found to be about 0.06 g.
17. 3. The solvent was removed in vacuo and the residue was purified on silica gel
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24. 5Na (M+Na) 467.183, found 467.182.