Regioselective Acylation of 2 '- or 3 '-Hydroxyl Group in Salicin: Hemisynthesis of Acylated Salicins

Regioselective Acylation of 2 '- or 3 '-Hydroxyl Group in Salicin : Hemisynthesis of Acylated Salicins

QC 20141205
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.

Ingår i:Chemical Research in Chinese Universities: Springer Science and Business Media LLC30:5, s. 774-7771005-90402210-3171

Av författaren/redakt...: Chen, Shao; Yuxin, Pei; Borg-Karlson, An ...; Zhichao, Pei

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