摘要
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-acetylsaliein(5a), 3'-O-acetylsalicin(gb) and 3'-O-benzoylsalicin(Sd) 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.
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-acetylsaliein(5a), 3'-O-acetylsalicin(gb) and 3'-O-benzoylsalicin(Sd) 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.
基金
Supported by the National Natural Science Foundation of China(No.31270861/C050204), the Agricultural Science and Technology Innovation Project of Shaanxi Province, China(No.2012 NKC01-12) and the Talent Start-up Fund of Northwest Sci-tech University of Agriculture and Forestry University, China.