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Regioselective Acylation of 2 '- or 3 '-Hydroxyl Group in Salicin: Hemisynthesis of Acylated Salicins
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2014 (English)In: Chemical Research in Chinese Universities, ISSN 1005-9040, E-ISSN 2210-3171, Vol. 30, no 5, p. 774-777Article in journal (Refereed) Published
Abstract [en]

Salicin-based phenolic glycosides(PGs) are important defensive substances against herbivore feeding and have good bioactivities. In this work, a novel approach for the synthesis of salicin-based PGs has been developed, by which PGs of 2'-O-acetylsalicin(5a), 3'-O-acetylsalicin(5b) and 3'-O-benzoylsalicin(5d) were hemisynthesized. The effects of acylation reagent, solvent and temperature on the regioselective acylation of 2'- or 3'-hydroxyl groups of salicin mediated by dibutyltin oxide were investigated. The optimal conditions under which the best regioselectivity reached for 5a-5d were discovered, respectively. Moreover, a tentative tin-oxygen coordination mechanism was put forward to explain the different regioselectivities shown under different conditions.

Place, publisher, year, edition, pages
2014. Vol. 30, no 5, p. 774-777
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-156996DOI: 10.1007/s40242-014-4041-yISI: 000344448400014Scopus ID: 2-s2.0-84909645087OAI: oai:DiVA.org:kth-156996DiVA, id: diva2:769007
Note

QC 20141205

Available from: 2014-12-05 Created: 2014-12-04 Last updated: 2017-12-05Bibliographically approved

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Borg-Karlson, Anna-Karin
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