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Number of results

Journal

2011 | 9 | 3 | 492-498

Article title

Epimerization, transacylation and bromination of dihydroquercetin acetates; synthesis of 8-bromodihydroquercetin

Content

Title variants

Languages of publication

EN

Abstracts

EN
Dihydroquercetin (dhq) and its 3-acetate react with acetic anhydride in the absence of a base catalyst to yield mixtures of partially acetylated products. Three new esters were characterized by NMR spectroscopy as dhq 3,7,3′-triacetate, 3,7,4′-triacetate and 5,7,3′,4′-tetraacetate. At its melting point neat dhq 3,7,3′,4′-tetraacetate is partially converted to dhq 3,3′,4′-triacetate and dhq pentaacetate by intermolecular acetyl transfer. Dhq 7,3′,4′-triacetate yields exclusively dhq 3′,4′-di- and 3,7,3′,4′-tetraacetate under these conditions. The acetylation/deacetylation reactions are accompanied by partial epimerization: 3 new acetates with 2,3-cis stereochemistry (dhq 3-, 3,7,3′,4′-tetra- and penta-) were identified. Dhq and its 3,7,3′,4′-tetraacetate undergo regiospecific dibromination at C-6 and C-8 with excess N-bromosuccinimide in polar solvents, and 6,8-dibromo-dhq can be regioselectively debrominated to 8-bromo-dhq with sodium sulfite.

Publisher

Journal

Year

Volume

9

Issue

3

Pages

492-498

Physical description

Dates

published
1 - 6 - 2011
online
22 - 3 - 2011

Contributors

  • Simon Fraser University
  • Simon Fraser University

References

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Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_s11532-011-0032-8
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