Synthesis of 1‐(β‐D‐ribofuranosyl)indol‐3‐acetic acid
Journal of Heterocyclic Chemistry (Impact Factor: 0.79). 03/2009; 23(6):1777 - 1779. DOI: 10.1002/jhet.5570230635
By condensation of ethyl indolin-3-acetate (4) and 2,3,5-tri-O-benzoylribofuranosyl-1-acetate (5), ethyl 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)indolin-3-acetate (6) was obtained in good yield. The indoline nucleoside 6 was aromatized to ethyl 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)indol-3-acetate (7) with DDQ. The treatment of the indole nucleoside with barium hydroxide and methanol gave the methyl ester 8, which was further treated in water to give the desired 1-(β-D-ribofuranosyl)indol-3-acetic acid (9).
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ABSTRACT: The linear synthesis of 1-(β-D-glucopyranosyl)-, 1-(β-D-galactopyranosyl)-, 1-(β-D-mannopyranosyl)- and 1-(β-D-ribofuranosyl)benzocamalexin was elaborated from indoline as a starting compound and corresponding pentaacetylhexoses or 1- O -acetyl-2,3,5-tri- O -benzoyl-D-ribose as suitable glycosyl donors.Collection of Czechoslovak Chemical Communications 08/2004; 69(8):1657-1674. DOI:10.1135/cccc20041657 · 1.14 Impact Factor
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