Regioselective O-alkylation of ascorbic acid for the efficient synthesis of lipophilic antioxidants

Synlett

Volumn , Issue 1, 1999, Pages 147-149

  Beifuss, Uwe ^a   Kunz, Olaf ^a   Aguado, Gemma Patricia ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Alkyl triflates; Antioxidants; Ascorbic acid; Ethers; O alkylation

Indexed keywords

ANTIOXIDANT; ASCORBIC ACID; ASCORBIC ACID DERIVATIVE;

ALKYLATION; ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032911813     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2522     Document Type: Article

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22. Satisfactory analytical (combustion and/or high-resolution mass) and spectral (UV, IR, NMR, and MS) data were obtained for all new compounds. Yields refer to purification by flash chromatography on silica gel.
23. 4 and concentrated in vacuo. The crude product was purified by column filtration on silica gel followed by recrystallization or by flash chromatography on silica gel.
24. 4 and concentrated. The crude product was purified by flash chromatography on silica gel.
25. 2) at rt and monitored by TLC. After filtration under Ar the filter was washed with ethanol. The solvent was removed in vacuo and the crude product was purified by flash chromatography on silica gel.
26. 6): δ = 14.29 (C-8′), 23.24 (C-7′), 26.34 (C-3′), 29.92 (C-5′), 30.03 (C-4′), 30.35 (C-2′), 32.49 (C-6′), 63.43 (C-6), 70.44 (C-5), 72.11 (C-1′), 75.82 (C-4), 122.08 (C-2), 158.68 (C-3), 169.93 (C-1).