Regioselective Acylation of 2 '- or 3 '-Hydroxyl Group in Salicin: Hemisynthesis of Acylated Salicins
2014 (English)In: Chemical Research in Chinese Universities, ISSN 1005-9040, Vol. 30, no 5, 774-777 p.Article in journal (Refereed) Published
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, 774-777 p.
IdentifiersURN: urn:nbn:se:kth:diva-156996DOI: 10.1007/s40242-014-4041-yISI: 000344448400014ScopusID: 2-s2.0-84909645087OAI: oai:DiVA.org:kth-156996DiVA: diva2:769007
QC 201412052014-12-052014-12-042014-12-05Bibliographically approved