first and efficient synthesis of 4-[((3,4-dihydroxybenzoyl)-oxy)methyl]-phenyl-β-d-glucopyranoside, an antioxidant from origanum vulgare

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ID: 210729
2016
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Abstract
4-(3,4-Dihydroxybenzoyloxymethyl)phenyl-O-β-D-glucopyranoside (DBPG, 1 ), a polyphenolic glycoside previously isolated from Oregano(Origanum vulgare L.) in 0.08% isolated yield, was synthesized in five chemical steps with 41.4% overall yield. First, 4-(hydroxymethylphenyl)-2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside 4 was obtained in 53.2% yield by selective glycosylation of 4-hydroxybenzyl alcohol 3 with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 2 in a mixture of chlorobenzene and aqueous CsOH using triethylbenzylammonium chloride (TEBAC) as a phase transfer catalyst. Then, this product was esterified with 3,4-diacetoxylbenzoyl chloride 7 to generate 4-(3,4-diacetoxybenzoyloxy-methyl) phenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside 8 in 95% yield. Finally, selectively global deacetylation of 8 was performed in a mixture of dibutyltin oxide and methanol under reflux to afford 1 in 94.8% yield.
Reference Key
yu-wen2016journalfirst Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors ;Li Yu-Wen;Ma Cui-Li
Journal meditsinskaia radiologiia
Year 2016
DOI
10.2298/JSC150205074L
URL
http://www.doiserbia.nb.rs/img/doi/0352-5139/2016/0352-51391500074L.pdf
Keywords
synthesis antioxidant glycosylation

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