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
复制标题
DOI：
10.1007/s40242-014-4041-y
复制
发表时间：
2014-05
影响因子：
3.1
通讯作者：
Chen Shao;Y. Pei;A. Borg-Karlson;Z. Pei
中科院分区：
文献类型：
--
作者：
Chen Shao;Y. Pei;A. Borg-Karlson;Z. Pei
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 for5a–5d were discovered, respectively. Moreover, a tentative tin-oxygen coordination mechanism was put forward to explain the different regioselectivities shown under different conditions.
