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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

First and efficient synthesis of 4-[((3,4-dihydroxybenzoyl)-oxy)methyl]-phenyl-β-D-glucopyranoside, an antioxidant from Origanum vulgare